lucky number six

After the aforementioned argument with my father the morning after date #7, I dragged my exhausted and slightly hung over butt to work. I don't remember what was on my mind that day, but it certainly wasn't that date. A curious coworker asked how the date went. I told her that he was very cute, and very smart, but I didn't have high hopes. 

So imagine my surprise when I leave work for the day and a message pops up on my phone: "Hey, it was fun meeting you last night. Let me know if you'd like to hang out again!" I responded quickly and affirmatively but forget about it because I had bigger fish to fry (this is the weekend of my big move, and the same weekend I learn a fun little fact about #4).

A day or two later, everything has died down, and I still haven't heard from him. I've already conceded to this being yet another false start before my roommate goads me into contacting him. "If you wait for him to text you you're just going to be disappointed. Again." And so I bite the bullet. We both have the same day off that week, and plan to meet for lunch in his neighborhood. 

I wake up that morning feeling pretty good. I'm using this as a second chance at a first date, only this time without the alcohol and added stress. I replayed the first date over and over in my head, but each time the memory became more and more hazy. I told myself again and again that something must have gone right, even if I couldn't remember it. I put on a nice clean dress and made sure my lipstick wasn't smudged before I hopped on my bike to journey (and maybe not get lost this time) to Bushwick.

As I locked my bike outside the restaurant and saw him walking toward me I quickly remembered exactly why I wanted some liquid courage the week before. We smiled and hugged and said our hellos, and I wondered (thankfully not out loud) if it would be appropriate to order alcohol at 12:30 in the afternoon.

On a number of occasions during lunch I caught myself telling him things I already said the week before, and not telling him things that I thought I'd already said, but had actually told that terrible first date #6 that same week (another reason why I will never ever ever go on two first dates in one week ever again, do you hear?!). I felt so much more self conscious on this Thursday afternoon than I did the week before, but this was only my second time on a second date. I was all too aware of how messy my hair might have been, how my lipstick might have been smudged, how the buttons on my dress might've been coming undone, and I tried so hard to sound fun and interesting and smart. So many times I couldn't tell if he was laughing with me or laughing at me, but after lunch he suggested we go for a walk.

And so I got a very impromptu tour of Bushwick. We wandered for two hours, mostly talking about our love for Doctor Who and other British programs. I felt that familiar ache behind my eyes, the kind of headache that appears when it's been at least five hours since my last dose of caffeine. I decided to ignore it, in favor of going up to his rooftop to share a few cigarettes and conversations about cats, parents, and tattoos. A few hours after that, he needed to go to bed, and so I left his apartment. I didn't realize until I looked at my phone how long I'd spent with him. He walked me to my bike, and thanked me for spending my day off with him. Due to both caffeine and sleep deprivation, I stammered some kind of response about how he has less free time than i do, so I should be thanking him for spending his more valuable time with me (I still cringe when I think about that, by the way). He looked at me incredulously and I said, "I'm really sorry--I think I have a case of the stupids." He walked me to the end of the block and we kissed goodnight. 

I'm not really sure how I made it home. It wasn't that late (only about 8pm or so), but between the lack of caffeine and food in my body, the fact that I made it back to my neighborhood (by bike) is a goddamn miracle. He texted me the next day that it was great hanging out, and I smiled to myself. I smiled for a fraction of a second, and then panicked. Is the ball in my court now? Is there going to be a date #3 (or, #7c, if we're sticking with my order)? 

Moving is a very particular kind of hell. It doesn't seem like it would be difficult, but it's a fate I wouldn't wish on my worst enemy, I'm still grateful that I had the help of my roommate's very patient father, or else I would not have been able to get my belongings from one place to another, even though the new apartment was less than a mile away.

But the stress of having to move 75% of my belongings and make a trip to Target (also known as the seventh circle of hell) before heading to a closing shift at work (all after getting less than three hours of sleep and reeling from a terrible fight with my dad) was the definitive catalyst for the situation I would find myself in later that night. 

Work was not going well. All i could think about was going home and crawling into my bed (even though the sheets were at the new apartment) and reenergizing myself for the rest of my move the next day. But none of that was going to happen. While on my break at work, I receive a text message from #4, whom I hadn't heard from in close to two weeks. He apologized for not staying in touch, as he had been out of town and busy with work. When I mentioned that I was working until well after midnight, he suggested that we hang out when I was done. "Oh," I thought to myself. "I guess we're back to this."

I could feel any glimmer of self-respect fade to nothing as I left work to meet him. As I waited for him on a street corner I told myself "This is what empowered women do. This is what empowered women do." While I waited I chain smoked my way through most of my cigarettes, and thought over and over again about giving up and going home. But I wouldn't let myself flake. My phone was about to die and I didn't technically have a bed to sleep on that night. When he finally arrived, I knew he didn't like that I smelled like smoke. I didn't say much as we walked back to his apartment. He asked if I wanted to get a drink, but I knew that in that specific state of mind alcohol would only make things worse. I felt irritable and impatient, but at least there was someone out there who wanted to see me.

In his bedroom, he interrupted what we were doing to ask about my life, how the new job was, etc. I tried to be nice. I wanted to ask "Is this really the appropriate time for these questions?" but instead I responded kindly and vaguely, and asked him about his recent trip. "New Hampshire sounds lovely. Do you have to travel a lot for work?" Without any hesitation, he said "No, I went with my girlfriend."I thought that was a rather odd joke to make while a half-naked female sat in his bed, so I laughed and said "Oh yeah, very funny." He maintained that he was telling the truth, and I said "You're joking" about four more times before I finally believed him.

He couldn't understand why I was so confused. "But... but..." I sputtered as he tried to pick up where we left off. I was not going any further until I got some answers. He told me she went to Los Angeles (where he went to law school), and I shouldn't be surprised as his OK Cupid profile said "Available" rather than "Single." He very clearly does not want to pursue the subject, so, with him assuming that I should have seen this coming and with me becoming more and more confused we continue. 

An hour or so later, I'm wide awake and as he sobers up he realizes how much this is bothering me. "Does she know about this? Is she okay with this?" I ask. He doesn't say yes or no, only "Well, she lives three thousand miles away..." 

I leave when the sun comes up. I grab my things and he says "We should hang out again soon. I've missed you." As I walk home I realize I left my jewelry and phone charger there. I pack my few remaining belongings at the old apartment and walk to the new one. As I enter the door, I greet my roommate with coffee and a bagel and "Have I got a story for you."

I would tell countless people that day what had happened. I needed every perspective I could find, because I didn't know how to feel. A friend from home told me that he sounded like a sleaze, and I shouldn't speak to him again. My roommate told me that I could do what I want, but he isn't allowed inside the apartment. I couldn't know if, at a weak moment, I would be okay with seeing him again. But I did know one thing: I needed those necklaces back. I called him, and walked to his apartment after quite a few drinks with my roommate. He gave me back my things, and told me we should watch The Wire together. As I was about to say goodbye, he said "I think this is the first time I've ever talked to you when I've been sober." I thanked him for meeting me, then turned around and walked home. Suddenly I wasn't so confused anymore.

Coming up next: I turn over a new leaf.

'Til then,

I woke up the morning of this date and my first thought was "I am never doing two first dates in a week again." I was exhausted. On top of everything else on my mind, I couldn't be bothered with trying to create another good first impression. I was especially discouraged after my less-than-mediocre first date from two days before. It looked like this young man wouldn't be too different. Like #6, he was a musician, and offered some great advice on tomato sauce. But he was younger (22 to be exact), and from a few hours away from my old upstate stomping grounds. His profile was about as sparse as mine, but he photographed well. He suggested we meet at a bar in Bushwick after I get out of work, and my only thought was that I literally had nothing to lose.

When nine o'clock rolled around and I left work, I had half a mind to cancel. I was supposed to start packing that night, and I had promised my dad I would give him a call. I reminded myself that I hate flakes, and this boy seemed like a nice person so I ran as fast as i could to the train to make up for the time it would take me to wander around like a lost kitten in Bushwick looking for yet another hole in the wall bar.

I was in the bar for barely thirty seconds before he walked in. "Ohh shit," I thought. "He's really cute." He was dressed very similarly to someone I would never like to think of again, and I could feel myself getting nervous. The timid voice in my head that squeaked "Don't be nervous! Just be yourself!" was quickly squashed by the much more assertive and authoritative "Don't listen to her! Drink ALL the drinks!" and I chose a beer with the highest alcohol content on the list. Two nights ago I had to drink until he became interesting, and now I'm getting a strong drink because this date is attractive? What am I thinking?

He insisted on paying for the first round, and I wouldn't let him (two months might have passed since I started this project, but don't think I've forgotten about my rules). He wanted to pay for round two, and I wouldn't let him. He told me about his job, a pastry chef at a famous New York bakery. We talked about what we studied, or desire to go eventually go back to school, and our experiences living upstate. 

I couldn't read him, and that made me so uneasy. As the alcohol reached my bloodstream I could feel myself getting stupider, and becoming more self-conscious, leading me to drink faster. We had a lengthy discussion about books and writing, and for the first time on a date we rarely talked about music (even though he was a classically trained musician), except for some brief explanations about what instruments he played. He seemed ridiculously smart, but not condescending (though he did kindly laugh at me for my penchant for ripping up whatever paper goods are within arms' reach). We laughed at each others' jokes, and the three hours at that bar went by quicker than i've seen a date go before.

He stepped away to use the washroom, and the bartender came over to clear our glasses, and to let us know they were closing. After apologizing for staying too long, I looked her in the eye and asked, "He's cute, right? I'm not just drunk, right?" As I started babbling about how this was a first date and I was really nervous and unsure of myself. She stopped me and smiled. "Don't worry, he is pretty cute but you're doing just fine." 

We left the bar shortly thereafter. "Be cool," I told myself, but I wound up walking in the opposite direction from the train station. He smiled, showed me where to go, and walked me in that direction. We hugged and said goodbye. I rode the train home and thought to myself that even if I never heard from him again, I hoped I didn't make a complete fool of myself. 

My dad would call me the next morning, angry that I'd blown him off for a date. "Well, was it worth it?" he asked, expecting another apology. "Yeah, I think it was."

Next time: That startling revelation i've been hinting at comes to a head, and I get another case of the stupids.

'Til then,

One morning, H sent me a text message to check in. I told her about the new job, and how I just signed a lease. We got to talking about an NYC-based dating project we both followed. You might have heard of it, 40 Days of Dating. I told her about my secret desire to start a blog about dating, to make all of these dates worthwhile in some way, and she was on board immediately. I was still a little hesitant, so I quickly changed topics to my date that night. She asked for the details--"what's the story with lucky number six?" I told her what I knew--he was 26, a native New Yorker, a musician, and he liked Vampire Weekend. We were to meet at a music venue on the Lower East Side to see a bluegrass guitarist. And that's all I knew.

When we met at the venue, I had two simultaneous thoughts. First, I was disappointed at how short he was. Second, I was angry with myself for caring. I was already irritable because of a ten hour day at work, but I ordered a glass of wine and felt really thankful we were watching a musician so I could rest my brain a bit before having to talk. 

After an incredible performance, we walked to another quieter bar for drinks and talking. I wanted to give this guy the benefit of the doubt. He was cocky, and a little dim, and wow did he love to talk. We mostly talked about music. We loved a lot of the same bands, though for entirely different reasons. He was very honest in telling me that he didn't really listen to song lyrics, but he was quick to name drop all the bands he saw "before they were cool." The way he spoke, the way he thought so highly of himself for being a native New Yorker, the way he was proud that he didn't read--every time he opened his mouth to speak he was begging to be mocked. He lived one neighborhood over from me, so we took the train back together. After we said our obligatory "have a good night, it was nice to meet you!" he suggested that we go to show together sometime. I said a hurried "yeah, okay, maybe, allright, etc.!" before I hurriedly walked home. 

As I turned the corner to my street, I thought of what an incredible waste of time my last two dates had been. I couldn't continue doing this if I was going to get mixed signals from the good dates and nothing but irritation from the bad. I pulled out my phone and texted H. "Sooo that blog idea? I'm in. Let's do this."

Next time: I find myself in my least favorite neighborhood yet again, I move apartments and get some startling news.

From the second I visited his profile I thought “this person seems too good to be true.” He claimed to be tall, Australian, a graduate student, and assuming his pictures were both recent and representative of reality, rather attractive. On top of all of this, I had initially visited his profile because he was my highest rated match within 25 miles. Now, I know better than to assume that match percentage is everything, but if I am on a site whose main purpose is reducing all the intangible elements of human interaction to a number that is supposed to be representative of how well the algorithm thinks you would get along, well, I am still going to put a little stock in it. Despite all that, I couldn’t bring myself to message him. I sat there with his profile open on my computer and all I could thing was “no way, there is nothing I can write which will make my face interesting enough for this guy to respond.”

Imagine my surprise when not only does he message me, he sends one of the most well thought out messages I had received yet. We move quickly from a discussion of the antique map exhibit in the Library of Congress to his problems getting settled in North America to him asking me if I wanted to get dinner and drinks in Columbia Heights with him the following Thursday. I didn't know it at the time, but this rapid fire subject switching would be both the norm for the night and the backbone of one of the best outings I have been on to date.

  I meet him outside of the Columbia Heights metro station, and, being new to the city I am mostly just happy that I found the place without incident. Imagine my surprise then when I realize he is actually exactly as he described himself. He greets me with a hug and starts talking so fast and with an accent so thick it requires all of my mental energy just to keep up. A location for dinner had not been settled upon before meeting so we opt to walk up 14th and end up walking into the first place that “looks good.”

  Sitting at a picnic table in the back of a restaurant which claims to serve something called “momos” the conversation is rapid fire and I don’t think either of us stops laughing for the good hour and a half it takes for us to eat and drink three beers apiece. Leaving the restaurant neither of us is ready to go home yet so he suggests that we walk over to the Columbia Heights 20-something mecca that is Wonderland.

  Part biergarten, part dive bar, part dance club I am overwhelmed an a little drunk when it finally comes time to order our last drink. The night gets a little choppy at this point but there are a few moments which stand out to me: while standing in front of the bar he picks up my hand and pretends to read my palm, he is shows me videos of his dog on his phone and the girls sitting across from us try to kill us with their eyes, when we are riding the metro home together and when I have to get off to switch to the red line he looks genuinely sad and asks what I am doing this weekend in a rush. The combination of physical contact and alcohol have left me a bit flushed and I can’t stop smiling, I say “text me” and rush off the train only narrowly avoiding loss of life and/or limb.

  I don’t hear from him the next day despite the fact that I was convinced the night before that that was one of the special dates which warrants a second date. I start to question myself and figuring I have nothing to lose text him asking if he wants to go to the Turkish Festival together later in the weekend. He responds with “I’m sorry, I can’t” and that’s it, I never hear from him again.

  Much like I imagine an encounter with an actual unicorn would be, our encounter was brief, magical, and when it was over I was left wondering if it really happened.

  Next Up: I almost kill my date. 

In the weeks that followed the second time I spent the night at #4's apartment, I managed to sign my first lease, begin full-time work at the new job, and even go on a few job interviews. I had all but given up on hearing from #4 ever again. It was no huge loss. Granted, it was nice to have someone to talk to every so often, and it was nice to be called pretty, but it wasn't worth the anxiety I'd manufactured for myself. 

I have a friend who is about eight years older than I am, who has lived in Brooklyn for the last six years and who has plenty more experience with OK Cupid than I do. Around this time I adopted her as my OKC guide and guru. I took each of her nuggets of advice with a grain of salt. After all, this experience is different for everybody, and it seemed like she felt far less of the same anxieties I feel over using the site. However one of her anecdotes came true--Fall is the time for courtship. Once the weather started cooling down, the messages started rolling in. I kid you not, on September 21st (the vernal equinox for those Earth science buffs out there), I received seven legitimate messages (i.e. messages I would respond to according to my own guidelines) from interested suitors. Good lord, I didn't even know where to begin. Most of the messages referenced the same parts of my profile--my devotion to Death Cab for Cutie, my semi-accurate description of what I'm doing with my life, and my desire for an easy and tasty tomato sauce recipe. 

I decided to respond to the message mentioning some helpful tips for a good sauce, and recommending I listen to Department of Eagles if I haven't already. He suggested we meet for a drink after the third message. It was a bit hasty for my liking, but I was feeling a bit burnt out from all this dating that I had become less picky. He sent me a text about a week later about meeting at a bar in Bushwick that Wednesday. 

I really didn't want to go. I did not know my way around Bushwick, I'd never successfully gotten myself to that neighborhood, and I'd never had a great time while there. As I expected, I got lost on my way to the bar. I overshot it about twice, and I really had to pee. 

He was cute, on time, and wearing a nice sweater. I had a brief moment of panic when he walked in the bar because I thought I had already forgotten his name, but it came back to me quickly. We talked about our jobs--he worked at an education startup and was getting ready to move to New Orleans. He didn't seem that interested in what I did. We talked about music, how he had been going to a lot of EDM shows. I, no longer caring about what he thought of me, declared that I hated EDM. He challenged most of my statements, usually with "why?" I liked that, it kept the conversation going. He asked me about my experience using OK Cupid, and seemed very keen on talking about all the strange women he'd gone on dates with. He was very inquisitive, almost to the point of being offended, regarding why I was so interested in getting a tomato sauce recipe. He accused me of using that as a gimmick for attention. "Well, duh," I replied. "That's how online dating profiles work. And clearly this tactic did its job." I told him that I love tomato sauce and would like to make it for myself, but I don't think he bought it. I tried to switch topics, I could no longer feign the confidence to talk about OK Cupid on a first date, but he insisted on continuing. After he asked me rather aggressively why I keep my questions on private, I responded rather aggressively that I refuse to talk about this anymore. After a lengthy conversation about our experiences with hallucinogenic drugs, he announced that he had to be awake at seven the next morning for work.  He walked me to my train stop, there was a quick hug and a "nice to meet you!" but neither of us was expecting a "let's do this again." 

I woke up the next morning to a half dozen or so other messages. My friend really wasn't kidding. 'Tis the season, I guess!

Up next: Two more first dates in a week--when will this insanity end?! And then, the boy #4 situation takes a turn for the weird. 

I created an OKCupid profile about a month before moving to DC with the intention of giving OKCupid a test run in my hometown before plunging myself headfirst into the DC online dating pool. I wanted to learn the unspoken rules of messaging on the site before actually meeting anyone because I am nothing if not a little neurotic when it comes to trying to fully understanding social conventions. Therefore, upon arriving in DC, I thought I had a pretty good handle on what made up a “good” message and what meant that a guy was showing actual interest while keeping the red flags to a minimum.

DIvdiv alogn - Naturally, when I was messaged the Arrested Development quote where Buster is made fun of for studying cartography (I mention geography in my profile) it does not take many messages before I have agreed to meet for coffee in Chinatown. I decided to view the date as a test run because, having never been on a date with a stranger before, I was positive I would probably manage to mess it up horribly.

My first rookie mistake was deciding to walk from Dupont Circle to Chinatown 90 degree heat while wearing a dress made of polyester. By the time I got to the coffee shop I was sweating profusely and my body had no intention of stopping. I also ordered a hot coffee because, I don’t know, I panicked?

I sat at a table facing the door while pretending to look at my phone and actually just covertly scanning every face which walked in while praying that I hadn’t developed visible sweat stains. When my date finally arrived we shook hands, he got a coffee, and we proceeded to stare at one another somewhat awkwardly and struggle to make small talk for the next two hours. Second rookie mistake: not drinking or being in motion. Whomever thought grabbing coffee was a good idea for a textbook “first date” has clearly never met me. Without the surroundings constantly changing or me being slightly inebriated by drink 1.5 there was nothing to pad the awkward pauses from being really, really awkward.

Rookie mistake number three: as most people who have ever meet me know, when I panic I usually start explaining the agricultural subsidy system and the finer points of corn farming in the US. So, when faced with awkward pauses instead of taking another sip of my coffee, I did that. Don’t do that.

In my defense, when I stopped talking and tried to ask this guy a question about school (he is a law student) or things he likes to do, or really any other topic, he would give me a one or two word answer and then he would stare at me until I started talking again. I think we were both trying to figure out the least-rude way to leave without totally offending the other person.

In the end, he decided that checking his watch, mumbling about a meeting, and then sprinting out of the coffee shop was the best and most mature way for a 25 year old man to jump ship. This is a point which I really do not think can be emphasized enough. He did not say goodbye. He literally grabbed his bag and ran out of the coffee shop as fast as he could. Lessons learned.

Armed with the confidence of someone who knows that it probably won’t get much worse than that, I checked my messages on the train home and vowed that next time I make sure that the date takes place somewhere with a liquor license.

Next Time: Australian graduate students? Yes, please. 

I started to panic when I didn't hear from him again. I felt like I was losing my mind, but that couldn't be blamed entirely on him. I was transitioning from my old job to my new job, looking for a new apartment, and I'd just lost a very influential former teacher back home. I had to isolate each anxiety. Was I actually interested in him romantically? He was a good kisser and fun to talk to, but something was still off. Was I panicking because I thought maybe I'd done something wrong, and that's why I didn't hear from him? I went over everything again and again, and nothing seemed wrong. Luckily I had a new job, an apartment hunt, and a camping trip in the Catskills to keep me from dwelling on this even more.

And then, as I started to write this off as another false start, he sent me a text on a Saturday night, maybe around midnight, asking what I was up to. I was at a bar, the same bar where he and I had our first date, celebrating finally finding an apartment with two friends. Coincidentally enough, he said he was heading there with a few friends anyway. My friends offered to stay and act as my wingwomen. I think they knew before I did what kind of situation I set myself up for. I was never the hook up type in college, but I knew as well as the next person what a late night text meant. And at that moment, that was all I really needed.

And then suddenly I found myself in a similar set up to the Saturday before. And the next morning, as I headed home with not even enough time to shower before I had my last day of work at my old job, I realized I could hardly classify that as a date. It was a little serendipitous that he would wind up at the same bar as I, but beyond that it was nothing more than a hook up. I never did the hook up thing in college. The few one night stands I had were so terrifyingly bizarre that I had zero desire to repeat the experience. My college was large and liquor-soaked, definitely not a dating school, and when it came to any kind of sexual desire for the opposite sex, I much preferred to pine from a distance. 

When I didn't hear from him, save for a text message telling me how many hairpins I left behind, I knew exactly what I had gotten myself into. I never considered myself the hook up type, but there's always a first time for everything.

Coming up next: I switch tracks and go on three more first dates before this situation blows up in a way I didn't expect.

'til then,

I can't say I woke up the next morning hungover and anxious, because I didn't sleep at all. Any optimism I had had been replaced by anxiety. I can't ever do something and not dwell on it--what it was, what it means, why I did it, etc. So kissing a boy I'd met twice certainly left me reeling. I didn't have a lot of room to let myself panic because a., I had to go to work the next day and b., there was very little to panic about.

Until the next day. He asked me to join him after I left work at a small get together at his friend's apartment in our neighborhood. In all honesty, I really didn't want to. I would rather never see this person never again than have to meet even more people and try to impress them too. I was all ready to text him that something had come up and I couldn't make it when I reminded myself why I joined OK Cupid to begin with. I'm trying to eliminate all of the weird anxiety I feel over really normal social situations. If someone invites you to meet their friends, the proper reaction isn't to run in the opposite direction. So I came home from work, cleaned myself up a bit, an biked on over because there was no reason to be scared. On my way there I remembered a party I went to a few weeks before. One of the hosts was really excited because the girl he met on OK Cupid was coming, and we were excited to meet her. I recoiled a bit and wondered "oh no, am I that girl? Am I the OK Cupid girl?" I tried not to worry about it because, once again, there wasn't anything to worry about.

I couldn't worry about this because I had enough on my plate already. I happened to quit my job that day, and I was about to start a new job the next day. When I arrived at the apartment and he came outside to greet me, I said "So I quit my job today..." And then I took another deep breath and got ready to meet the friends.

Many drinks later, the conversation turned to online dating. "That's how you met, right? On OK Cupid?" Stop it. You know damn well that's true. But I smiled sheepishly and nodded. I realized I was in the company of people who used the site regularly, and I had no reason to be bashful about it. This would be the first of many conversations I would have about OK Cupid (I almost want to start a separate blog chronicling all of that). Everyone there was a few years older than I was, but as the afternoon turned into the evening, I felt more and more at ease. We walked as a group to a bar around the corner, and as the evening turned into night he and I became much more affectionate and before I could feel self-conscious about PDA in front of people I'd just met, it was just he and I. 

And then it was just the two of us at the entrance to his apartment. I couldn't let myself wonder if this was the right thing to do when he asked if I wanted to come up. If I was to think about it--to consider if I was okay with sleeping with someone I'd met on the Internet, in the most inorganic way possible,not to mention if it was safe to act as such, even though I had to be at my new job at 8 the next morning--I'd be standing in that doorway until the sun came up. So I smiled and said "yeah, okay."

I left his house at dawn the next morning, with only enough time to shower and change clothes before I had to start my first day of training. When I didn't hear from him the next day, or the day after that, I started to panic and told myself not to worry. When I had dinner with friends and they asked "so is he your boy now?" I said something I would find myself saying again and again. "Please. Let's not get ahead of ourselves here."

Coming up next: I can see what this will turn into, and I'm okay with that. Also, I have first date #5 and 6, but we'll get to that.

'til then,

The idea of online dating always appealed to me. I hate leaving any aspect of my life up to chance and if there is a website out there that is going to filter through a population and then give me a percentage of how well it thinks I would get along with a member of this population I am going to sign up. The closest I have gotten to a romantic relationship in the past year has been turning to the person I had been talking to any given Friday night and saying “I have finished my wine, do you want to get out of here?” Clearly, there were some flaws in my approach. Signing up for OkCupid was (and is) my way of saying that I am ready to close the book on that chapter of my life and to start learning first names again.

  After a post-graduate summer of unemployment, general self-doubt, and feelings of failure, I finally landed an internship in Washington, DC. It was with the confidence of someone who finally felt like she had something to talk about on a first date other than the college that I went to work piecing together a profile. I started a little early, using my hometown as a practice ground, but I didn’t commit to the whole online dating lifestyle until I finally found myself friendless and alone in a new city. What is the point of all these free museums if I don’t have anyone to visit them with?

  As I familiarized myself with a new internet subculture, a few rules and patterns started to emerge in how I used the site:

If I am going to message someone I make sure that the message reasonably well thought out and reflective of what it was about their profile that piqued my interest. If I am going to screen my messages and refuse to answer anything along the lines of “hi” or “I like your lipstick.” then I have to expect that everyone else will do the same.

I will not continue to message with someone who asks me out in the third message. If you refuse to chat with me over the internet, I refuse to chat with you in person.

They need to be in the metro area. I haven’t decided if this includes Baltimore yet or not, probably not. Unless they have an aquarium membership, then I would definitely consider it.

I will not exchange numbers until we have already agreed to meet, and chances are I will fade if one is given without reason. Seriously, who just goes around giving their number out to strangers without a reason?

  Armed with a list of best practices for online dating and an open mind, I prepared myself to learn all that I can about what DC has to offer in terms of eligible bachelors and possibly about myself along the way.

I took the "we should do this again" as an opportunity to take some initiative in my own life. Six weeks in the city had left me a lot more confident than when I started this "dating" business. I also wanted something to show for all of the time I'd put into this whole endeavor. I had a brief conversation with an upstate friend who wanted to check in with me to see how the OK Cupid life was going. I told him the same stories I'm telling you, ending each one with "and I never heard from him again." He called New York "the city of first dates," and I wholeheartedly agreed. But I wasn't going to let that title win this time. 

I briefly wondered if there was some kind of statute of limitations for how long I should wait before I text regarding a second date. After all, I was a seasoned first date-er now, but a second date? Strange and unchartered territory. Maybe I was exhausted from work, or maybe I felt stressed from having to find a new apartment, but for whatever reason I wasn't nearly as anxious about planning this one as I had should have been. A quick Google search and a few text messages later, I'd found a cool show at a Manhattan venue and whaddayaknow, I had a second date planned for a few days later.

I knew there was no way I wouldn't be nervous, but I wouldn't let myself turn into a wreck. I channeled whatever nerves I felt about going on a second date into feeling  nervous about not getting lost on my way to the venue. I wouldn't let myself spend hours in front of my crumbling dresser picking out an outfit. Instead I left my apartment extra early, caffeinated myself to the point of tremors, and tried to read by the East River until it was time to venture into Manhattan. 

This is my first foray into writing about dating, and I could very easily turn this into a concert review because I'm far more comfortable talking about music than confronting my own feelings (hence why I started this project). I'll leave it at this--the music was great. As is wont to happen when I go to shows, I wound up liking the opener more than the headliner. But the music was only a secondary aspect of the night. It was an obvious catalyst for conversation that we didn't even need. We had far too much to talk about, and left the venue singing Postal Service lyrics at each other. When we wanted to head back to Brooklyn we'd had a few too many whiskey and ginger ales and were still a little too new in town to make that an easy experience. But somehow we made it back to our neighborhood, where he kissed me goodnight as we parted ways. As he said goodbye, he asked if I'd like to meet a few of his friends the following Saturday. For the first time in a long time, I didn't even think before I said "sure!"

I got home, where my first course of action should have been to put myself to bed. But I was too giddy, and too wired, At the time, I lived with four other people who were all awake, waiting patiently in the kitchen to hear about my date. I probably gushed a little too much, or maybe I was entirely incoherent. But I didn't sleep at all that night. My insomnia was back with a vengeance. The next day, before work, one of my roommates sat me down to try to offer some advice about dating this particular boy. I laughed and said "let's not get ahead of ourselves here."

Coming up next: I force myself to face another one of my many anxieties, and I find myself becoming "that girl." Stay tuned!

A week and a half after that bike ride, I found myself in a very strange place. I became more and more frustrated with my then-job, and started feeling more and more homesick for my college town, a place I couldn't leave quickly enough when I moved away in July. I felt anxious and irritable and very, very sad. I missed my upstate friends, my upstate house, and my upstate coffee shop. When I thought I couldn't feel any more unhappy about things I told myself over and over again didn't matter, my "brief summer fling" (Remember, the one I rarely saw because he lived an hour away) text messaged me that he was visiting Syracuse to watch a mutual friend play a show, and I realized I might miss him most of all. The entire situation made me feel very weird, and I felt weird about feeling weird. Add to that my continuing anxiety regarding online dating, and I found myself in a very deep and dangerous brain k-hole I couldn't climb out of.

Amidst this mess I started messaging a 24-year-old law student on OK Cupid who opened the conversation with a few comments about Jeopardy and Bright Eyes. My heart wasn't really in it, I was far too focused on wallowing in my own misery, but after one particularly rough night at work and a motivating conversation with my roommates I agreed to meet this young man for a drink the next night at a bar a few blocks away from my apartment. 

I was too tired to be nervous for this date. I threw on a dress, put on some lipstick and thought "well, might as well get this over with." I noticed on my walk over there that I was breaking a few patterns I'd fallen into since starting this whole thing. First, it wasn't a Wednesday. Second, I didn't get lost on the way there (a small detail, but it made me look more like someone who knew what she was doing and less like the new girl at school who accidentally wanders into the boys' bathroom). Third, this person had been living in the city for even less time than I had. I didn't even overshoot the bar like I usually do. These are all minor things, but maybe I was getting the hang of this after all.

We immediately started talking about our experiences living in the city. He was a midwest transplant as well by way of Los Angeles, and only living here through November. We swapped our best concert stories, and he told me he was impressed that I actually finished Infinite Jest. We watched the same television shows, read the same books, and though he made fun of me for my obsessive dedication to Death Cab for Cutie, he complimented my "nerd-like knowledge" of music. We talked about growing up in the Midwest. Apparently his friend lives across the street from my old house upstate. I felt the familiar sting in my throat from talking too much. We talked non-stop for over three hours, until he realized that he had to be up early for work the next day. 

I felt very at ease. Maybe it was the fact that I wasn't nervous to begin with, maybe I enjoyed talking to someone who wasn't a roommate or a coworker, or maybe it was the two very strong beers in my bloodstream. Whatever it was, when we parted ways I felt like I had made a new friend. I barely walked in the door to my apartment when he texted me that he had a lot of fun and we should try to go to a show together. For those of you keeping score at home, this was my first opportunity for a second date. I responded with a quick "yes, definitely!" and wondered if it would actually happen. Suddenly I didn't feel so homesick anymore. 

Coming up next: My first second date! And after that, things get... interesting. Stay tuned!

Seven days had gone by, and not a word from #2. That ship had sailed, and I was already on to the next adventure. One night (or early morning, depending on your sleeping habits), while trying to fall asleep, I scrolled through that day's batch of OKCupid profile visitors. A message popped up, thanking me for mentioning the movie Once, as he thought it was a great film but hadn't given it much thought since he first saw it. i do my most courageous OKCupid-ing when I've had a couple of drinks in me, so I responded immediately. From there, the messages took the normal trajectory they take with me--chat about where we're from, shared interests, etc. We talked about The Swell Season and The Pixies, before he asked what my favorite music venues were. He didn't respond for awhile, and I wrote the interaction off as another false start. But two days later, as I was (once again) trying to fall asleep after having a few drinks, he sent me a message saying there were a few places he'd like to show me. I sent back a one line response: that I was free the next night, followed by my phone number. He told me to expect a call.

Needless to say I was a little distracted at work the next day. I had an eight hour shift with two coworkers who gave me that pep talk for my date the week before, and they were sorely disappointed when I said that he never contacted me again. But I followed that with "but I have my third first date tonight," and their ears perked up immediately. One coworker was a recent Brooklyn transplant like myself, but too wary of Internet dating to ever give OK Cupid a try. The other was a seasoned user, both when he lived in Chicago and now. He held out his hand expectantly, and I handed him my phone with the app already open, and he critiqued my profile from top to bottom. My supervisor was too amused to reprimand us for having our phones out on the floor, and upon seeing what a nervous mess I was over the pending First Date #3, she even let me sneak off the floor to call this guy back. After all was said and done--after all my giggles and shrieks and "I'm not crazy, I promise!"s to my coworkers over something as simple as planning a date--there was a plan: a bike ride through the southeastern part of Brooklyn.

We met outside Barclays Center. I was immediately nervous--he was definitely the best looking out of the few dates I'd been on. The plan was fifty percent bike tour through Brooklyn, fifty percent bar crawl. I became more nervous. I'm a cycling fiend, but I only ride by myself. I'm a little reckless and I ignore all traffic laws, and to anyone who doesn't know me it probably looks like I never learned to ride a bike properly. 

But the voice in my head saying "stop being stupid" was thankfully much louder than the voice listing all the reasons why I didn't want to be doing this. I'm glad the voice of reason won, because it was a great bike ride. He went to high school in Binghampton, and to college in a small town near the Adirondack mountains, so we had plenty of central and upstate New York heritage in common. He too had to work a service job while looking for work in his own field, only he couldn't wait to get out of New York. 

After I mentioned how much I love the East River, we rode through Brooklyn Bridge Park. We stopped at the gate before the water, and I looked across at the Manhattan skyline. I looked to the left and saw the Statue of Liberty. He couldn't believe that I'd never seen it before but I wouldn't let myself feel weird about it. We biked from one bar to the next and without really trying I felt myself getting more and more intoxicated. I wasn't worried about doing anything foolish (though I did say some very stupid things), I was more worried about not remembering anything for my own personal records. I knew for sure that I should have kept my drinking to a minimum when I started to complain about my abundance of orthodox Jewish customers at work, only to find out his family is very very observant. He wasn't offended, but I still felt terribly stupid. 

Though this entire ordeal started with a message from him about music, we didn't talk about it once. Instead we exchanged book recommendations, what it was like to live upstate, and what it was like to grow up in vastly different Jewish households. I felt more at ease as the night wore on. The part of me that wants to believe I'm becoming a real adult would probably blame that on maturing, but I'm pretty positive it was just the alcohol talking. We parted ways after about four or five hours. We shared a hug and a smile, but no "we should do this again." 

I didn't think too much of it then, but over the next few days I found myself thinking that maybe possibly probably I want to hang out with him again. Well, this was new. Was I attracted to him? Did I just want to have someone to ride bikes with? Was I starting to get bored? I didn't know the answer, so of course I started to panic. After my friends, roommates, and a few coworkers all rolled their eyes and said "just text him already," I finally did. Nothing too complicated, just a thank you for the tour, in the hopes that even an innocuous message like that would give him the hint that I'd like to see him again. He sent a friendly response but zero indication that he would like to see me. "Well, of course he didn't, you dummy," offered my friend. "You didn't say anything about hanging out!" 

And that's when I learned a very true and obvious lesson about implicit versus explicit. For my entire life, everything I've ever said has always been very implicit--drenched in implications and subtext, just waiting for someone to infer what I'm trying to express. At that moment I realized (or at least started to) that if I wanted to get anywhere in life, especially in this tricky dating mine field, I can't pussyfoot around anything. I'm not arguing the tired and clichéd "boys are so stupid they wouldn't recognize a hint if it danced naked in front of them." Instead I'm beginning to understand that if I want to live that true adult life I'm trying to find by tackling the dating world, I need to start by communicating like one. 

As I expected, I never saw him again. I'm sure it was for the best. I doubt we had much in common, but that's the funny thing about me when I drink whiskey--suddenly everyone should be my best friend.

Coming up next: Sunday becomes the new Wednesday, and I start a new chapter of my New York life as I get a new job and have my first second date. 

'til then,

Date number two took place exactly two weeks after the first. It seemed as though Wednesday was turning into date night. I immediately responded to his message inquiring which part of Chicago I was from, as he used to live there for awhile as well. I was feeling rather rather terrible that week, having just learned I needed oral surgery on top of getting a traffic ticket, and some Midwestern homesickness started to set in. Meeting someone from my old stomping grounds would be just what I needed to get out of my funk.

The planning process for this date forced me to face one of my greatest anxieties: talking on the phone. We exchanged numbers over the OKCupid message, and he insisted on calling me to make plans. Of course I Googled his area code. LA. I was of course skeptical, but I'm doing this to get over my irrational fears and judgments so I had to swallow that skepticism and meet this boy. We made plans for sushi and wandering in Williamsburg, standard "date" activities. It was all very benign and innocuous, so why was I even more nervous than I was for my very first date? As I left work that evening to race to north Brooklyn, my coworkers were shouting words of advice after me, such as "remember, don't put out!" (thanks for caring, guys). I thought about why I felt nothing about my date the week before, and why I had half a mind to call this young man and cancel the whole operation. The week before was me just getting my feet wet. But this being my second time, did that make me a "dater" now? Was I turning into a person who dates? I thought more and more on it as I raced from the Q to the L, trying not to trip in my boots and sweat through my dress. I walked up the stairs from the subway, took a deep breath and told myself to not be such a baby. I was fine.

Having dinner with him forced me to face yet another irrational anxiety--eating around other people. A (now dormant) eating disorder from my high school days had made me very uncomfortable with eating around other people, especially people I didn't know. It hardly came up as a problem in my day-to-day life, and that would be the night that I would quell that fear. 

We talked so much over dinner that by the time we were done I started feeling the beginnings of a sore throat. I knew that was a good sign. We wandered up Bedford, and then toward the water, and there was never a moment of silence between us. He was a musician, a writer, a comic book nerd, and horror enthusiast. Like me, he was an only child, and Jewish, and he was a smoker, and never slept. Unlike me, he was a college dropout, and he didn't drink. We liked the same bands and the same books and we both never slept and we made the same jokes. I followed ninety percent of his statements with "Ohh my goodness... me too." We swapped Holocaust jokes and talked about our respective desires for a giant in-home library. After dinner, walking along the East River, and splitting a Twix bar, we parted ways because all of a sudden it was two in the morning and I had work the next morning. As he got off the train he suggested we do this again, and I told him to call me, but he never did.

And I'm glad he never did. As much as we connected, he reminded me too much of all the parts about myself I didn't like, and he shared so many qualities with my upstate New York "summer fling" (whom I still talked to constantly) that I very much missed that I couldn't put myself through trying to build any sort of anything with him. I appreciated the opportunity to meet someone new, but it was like going on a date with a funhouse mirror. Our qualities were so similar, but in such a distorted fashion I felt spooked. Oddly enough, I didn't have any trouble sleeping that night.

Up next: Wednesday night continues to be date night for me as I take the greatest bike ride of my life, and after that I experience some good old fashioned Midwestern optimism (and ignorance).

'til next time,

We had planned to do a mini-bar crawl in our square of Boston. As I had just moved to Boston a few weeks ago, I didn't really know the ins and outs of the bar scene yet, and I was eager to explore. 

The funny thing is that I'm still kind of sensitive to the situation, and I'm slightly embarrassed to tell my roommates, "Hey, I'm going to hang out with this guy I met online, but don't worry, it's probably safe" so I've been using one of my friends as a cover. 

As I headed out the door at 10PM on a Monday night, I yelled, "I'm going to hang out with E at a bar! Bye!" 

So it's not like I'm not telling them where I'm going...right?

Anyway, I met him at one bar, already drinking some fiery tequila concoction. We go over our respective weeks. The sweet thing is that he occasionally pipes into my story in order to establish that he's remembered things about me, like "Oh, your favorite color is red, right?" or "You painted your nails. Weren't they grey before?" It was all so sweet and flattering. 

We headed to the second bar, which he said was his favorite and also a bit of a dive. He greeted the bartender and we both got a gin and something or other. The bartender gave us a smile and said it was on the house. Nice guy. 

This bar was probably the size of my bedroom, packed with tons of young adults, mostly college kids. The only thing in the back of this small room was your typical shooting game. One of the guns was clearly broken, sadly hanging out of its holster. He suggested that we play, and apologized for how good he was going to be, and then for how embarrassing of a skill it was to have. He effortlessly shot down beast after beast, and I would occasionally hit...something. 

Onto the next bar, the next drink. We went to a little underground bar, completely undetectable from the street. It was fashioned like a 1920s saloon, with the staff dressed in suspenders and flapper dresses. I ordered some drink with whiskey, and he ordered something with absinthe. We watched another couple nearby, obviously on their first date. This was when the drinks started hitting me. I was in that rosy state where everything was warm and inviting. Fortunately, it seemed like my date had been in that place for a while before me. He complimented my quick drinking ability, and I thanked college. 

We soon became bored with the semi-empty, eerily quiet atmosphere, so we headed back to the dive bar. We were walking down the street, and a homeless man told me I was pretty. I brushed it off, but my date replied, "I know, she's gorgeous."

Uh.

Um.

Well.

...

We were almost at the dive bar when he spun me around. It was that moment. We were supposed to kiss...and so I did. I went with it. 

And that's how we ended up in his apartment, and that's how I ended up having an adult sleepover. Because I went with it.

I woke up the next morning to my alarm that I had prudently set, because I had work...because it was Tuesday. I gathered my clothes, grabbed my purse, and headed out. Thank God he only lives a few blocks from where I live. It was definitely the most legitimate walk of shame that I've ever walked. I didn't look too out of place, but you could tell that I wasn't heading to work. 

I walked into my apartment, showered, and laid on my bed. Everything about that night had gone well, but something was bothering me. Something wasn't clicking, and it should be. He was sweet and funny and we meshed well, we liked the same things...what was wrong with me?

I headed out to work, feeling a little bummed. Later in the day, he messaged me and asked how I was doing. We bantered a bit until I had to actually start doing work.

I started talking to other people on OKC, wondering if my heart was even in it. Could I go around "dating" people without investing too much of myself? This is the first guy, and already I'm having feelings of guilt, like I'm doing something wrong.

Oy.