💕 How did they both realize “oh wait, this is actually love”?

Ash finds himself often falling in love but not acting on it, preferring to focus on his career. At least until he is forced to retire due to an incident with the Team Rocket Trio, with May was one of the last companions he had traveled with before then. So naturally he had quite the long lasting love for May. He'd realize that what he felt was love rather quickly after retirement.

For May, she tends to experience sexual attraction long before romantic attraction, and this is definitely true when it comes to Ash. I think it takes years for the romantic desire to set in, partially because of events I will discuss more of later.

🌹 Who fell harder & who fell first?

Depending on what you mean by falling first, it could be argued that either fell first. In AG001, how May reacts to Ash joining her definitely is easily interpretable as attraction of some sort. Combine this with what I said, you could say either fell first.

As for who fell harder? I think Ash would, as Ash is definitely a lover, despite common perception. That being said, I feel my answer is still more because of May being aromantic than Ash necessarily falling harder than most people.

🎶 What’s their song - the one that makes them both tear up / grin like idiots?

Oh good this is one of the few ships where I don't have to make something on the spot for an answer and it's more based on my personal Advanceshipping experience lmao

Sk8er Boi by Avril Lavigne is that song that makes them grin like idiots. I remember watching an AMV of the ship back in like 2007 or 2008 because it was my OTP when I was 10. I have associated the song with Advanceshipping ever since.

💔 What’s the one fight that almost ended them?

So the TRio basically kills and revives Ash before he and May even meet. Meanwhile, May ends up befriending the TRio on account of... well in canon she falls for Harley way too many times.

So while I don't have a scene in my head about that yet, the fight that'd have nearly ended them would be related to this.

Based on the timeline in my head right now, this probably will actually nearly kill it before it begins.

😳 What’s the most embarrassing thing they’ve walked in on the other doing?

So Ash actually has his Pokemon taken away before he meets May, and during the trial that caused this to happen, Ash developed a delusion where he legitimately thought he was a Pikachu. I think May could have walked in on a similar situation, and might have sort of freaked May when they were travelling.

When Ash came to, he was certainly embarassed. Thankfully, May also knows how to use AskJeeves or AltaVista or whatever was the big search engine in the 1999 (which is when I have the AG arc tenatively taking place) was and realized that it was something horrible, but also probably not his fault.

I'd imagine on the other way around, it could be when May is younger and starting to develop hair in unusual places for a cis woman, as I see her as having PMOS on account of I have it and have long felt that May would share a body type similar to mine, and if it's anything like my experience she'd be starting to have symptoms when she's travelling with Ash. This is less something Ash walked in on and more May not knowing how to deal with testosterone-based puberty. Being an intersex teenager is embarassing like that sometimes.

😏 Who is bolder in public (hand-holding, kisses, etc.)?

May, very much so. While May doesn't often catch romantic feelings, she adores romantic actions. She probably does more than a lot of alloromantic people, if I'm being honest.

🖤 What’s the darkest “we’ll never tell anyone” thing they’ve done together?

This one was the hardest one by far lmao

I think for them, it'd have to be when Ash had to leave Hoenn due to not having Pokemon to challenge any gyms due to his license being stripped. I think something would have happened that would have been of this nature. Probably a heart to heart, and both parties telling vulnerable secrets.

💞 How do they act when one of them is sick?

Ash is heavily traumatized with a traumatic brain injury due to him being killed and revived. May experiences chronic illness (as a nod to both KAORI's situation as well as an attempt to parallel Wally, as, while Wally exists in Shining Justice, I feel May to be the parallel to Pokespe!Wally while Drew is the parallel to Ruby) as well as mental illness. This is to say that both parties are quite familiar with the other being ill, as it's an unfortunately common experience.

In general, May enjoys being a caretaker. Because of the nature of Ash's condition and May's own tendencies, there just isn't much ofa difference between how May treats Ash when he's well and when he's sick.

When May is sick is a different story. When they were younger, Ash was less patient with May's frequent illnesses, particularly their toll on her ability to walk at the pace he preferred, on account of Ash's own condition worsening and making him more impatient. As they get older, I do feel Ash does become more understanding, at least as much as he's able to.

🌿 Do they want kids/pets/plants together? What do they name them?

Okay so they actually do have kids together in Shining Justice somewhere down the line. The background is that a friend of mine designed some original characters several years back for a different fandom that I wanted to appropriate for May fanchildren as they looked like they could really be May's children, especially with how I view her. My friend approved of the idea, and I later asked her what her favorite Ash ship was and she said she liked Advanceshipping best. So the designs were appropriated as per Advanceshipping, as the designs wouldn't change much, if at all depending on who their father is. If anything, Ash being the father makes the most sense!

Their kids' names are Meira and Jazmin. They wasn't exactly planned, at least with my current plans, but they love them, and May loves them as much as the Contestshipping kid that also exists, Lina. In regards to Pokemon, Meira specializes in dark types while Jazmin prefers water types. Not sure what their trainer class will be though.

💥 What’s the biggest risk one of them took for the other that the partner didn’t find out about until much later?

It'd be on May's end. May is part of the friend group of the Team Rocket Trio for years, and it's a kind of culty environment that has them putting her down. She'd not defend Ash for years out of fears of them coming after her, but one day, she does.

It'd be a big part of her social circle, and while Drew would stick with her, many would not.

🌸 What nickname do they have for each other that would mortify them if others heard?

Neither are particularly academic, even before the incident in Ash's case, and I'd imagine it's a sensitive point for both of them. However, they'd probably call each other "dumbass" or "idiot" or something like that in a sort of reclaimatory way.

If it slips in front of someone else, it'd probably embarass the absolute hell out of the other.

🌌 What’s their “we made it through hell” memory they’ll tell their grandkids?

Damn I need to actually write out the fics huh lol

Because yeah, their story of such a nature will likely be part of the fic. I don't even know what it is yet, honestly. I just know that it definitely exists.