the first time rose landry dates a gay guy, they're babies still figuring out how to be people—she figures out this whole dating thing is something she wants to get better at. he figures out that he's gay. they awkwardly and embarrassingly part ways the way you do when your first attempt at dating fizzles.
the second time rose landry dates a gay guy, it starts the same way. still in theater high school. neither of them know he's gay at the start of it. but crucially, the guy figures it out first and, for whatever reason, lets it go on way too long. rose is fully in love for the first time, and that compels her to ignore/deny the fact that he's gay after she figures it out. he has to be the one to end it. it's pretty messy.
the third time rose landry dates a gay guy she's moved to LA and they're both hungry young actors desperate to make it but, crucially, she's better than he is. and he knows it. he knows he's gay from the start. but he's, idk, the theater kid equivalent of a log cabin republican, or else/also an intense career and social climber who will do anything to get ahead. and being seen publicly with rose (not yet Rose Landry™, but anyone with eyes in the business can tell she'll get there) can only help him get ahead. she figures it out before she catches real feelings, but it is a pretty damaging experience.
the fourth time rose landry dates a gay guy, thank GOD, it is miles. if not for miles rose would not be the person who (we'll get there) could be kind to shane when he needed it most. miles, i have decided, is the male lead in the Not!-the-hunger-games movies that turn rose into Rose Landry. miles knows he's gay, and as soon as they become the equivalent of good-coworker-friends, he makes that clear to rose. he's not publicly out: he's young. this is his first big break to rose's second, and—take a moment to try and remember the insanity of the hunger games press circus, okay? second only to twilight and maaaaybe harry potter?—in the middle of the most intense media scrutiny of his young life is Not the time to come out publicly. the two of them get along like a house on fire and have completely insane on-screen chemistry, so when they are, ahem, encouraged to do a showmance during the shooting and press for the trilogy of movies, both of them shrug and go for it. they REALLY go for it. full court press. they also frankly have sex a couple of times just out of fun and affection, and it is some of the best sex of rose's life so far. their public breakup is amicable and they remain dear friends, as we see in the show. they keep getting cast together, too, because, well. insane on-screen chemistry. miles comes out publicly somewhere in all this.
the fifth, sixth, and seventh times Rose Landry dates a gay man, she's pretty peeved about it. it's all in her L.A./hollywood circles. all what, ten years prior, homophobes would have described as metrosexuals, sure, but they're in l.a.! that doesn't mean anything! they approach her, they pursue her a little, they're hot, she's interested—and it becomes clear a few weeks into it that they fully were looking for a beard but, crucially, Didn't Fucking Ask. they just led her on. maybe on the fifth guy, rose tries, still, because well, the sex was good with miles, and they're funny enough, but the memory of third guy rears his head and she realizes it's also about them using her fame for their own purposes. and the sex sucks. and he's not really interested in her as a person. kicked to the curb. sixth guy she doesn't let get past three months. seventh guy she gets pretty fucking angry at, semi-publicly, and their torrid breakup ends up in the gossip rags, and it only fuels her rage.
all this time she is having good-sex-but-emotionally-unfulfilling one-night-stands. there's, hmm, one and a half relationships with straight guys who are a little douchey, as it turns out, and also wanted to use her to raise their own profile. all this time she is still the little 14-year-old rose who figured out she DOES want to date she DOES want romance. she wants a man who wants her.
jock! not involved in hollywood at all! not even metrosexual! genuinely interested in her as a person! they text! they bitch about work! they gossip about hockey! there's an intense emotional connection there!
they have sex for the first time and—well. okay. he's still a jock, rose tells herself. a hockey player. his frame of reference for sex and relationships thus far is wags and puck bunnies. maybe there's a learning curve? surely shane hollander can eat up a learning curve in no time.
emotional connection is still there. they have sex a second time. rose feels a pit of dread in her stomach. she can tell he doesn't want her. oh god. he DID approach her at the bar—it seemed accidental, but if he's just trying to use her like the last few guys, maybe that was an act. maybe he's been acting this whole time. oh god.
she introduces shane to miles. doesn't even have to tell miles why, miles knows. miles doesn't even have to say anything back to rose after meeting shane—just gives her a Look. oh no. oh god. not again. some fuckwad knowingly using her as cover Without Asking, Leading Her On, with a side of This Helps His Career. again!! for like the fifth time!! what is it about her? I think all the questions we have about Rose Landry, dater of gay men, rose landry has also asked of herself. with no clear answers, because I also think she struggles to identify or develop a core sense of identity outside of her work.
so i think everything that happens after that in her relationship with shane—the dancing at the club with miles, the third time they have sex, and the first, mm, three minutes of their conversation at the restaurant—that's rose being mean. that's rose being SO mean to shane, on purpose. because Fuck This Guy For Doing It To Her AGAIN.
those questions rose starts off asking shane—holy shit, guys. rose, of Hockey Playing Brothers, Detroit Fan Fame, knows damn well that there are no out hockey players. she is asking to make shane uncomfortable. she is asking to make shane feel genuinely terrible, the way he's made her feel genuinely fucking terrible. she is doing this in a public place as a threat—blow-up fight with number seven taught her the power of that one.
but because rose is not stupid, she immediately clocks shane's reaction to this set-up after the gay hockey player question. first of all, he doesn't see the set-up for what it is. a guilty conscience would be all over this if he'd done this on purpose. what she's seeing from him is shame. shame and a bit of fear. part of this is that she's relatively smart and an actor, part of this is that shane starts obviously tearing up and looking miserable.
she catches this and immediately pivots. aw fuck, she thinks to herself. this is Not like five/six/seven. this man in front of me is still at, like, one or two levels of self-actualization—except, she already knows but repeats to herself, because this is why she was angry enough to pull this stunt with shane, except that she likes shane about as much as she likes miles. they ARE socially compatible. they DO have chemistry. just not sexual chemistry. this man thinks he can actually make this work because he hasn't, what, admitted to himself he's gay yet? that's so sad! at our age! (rose crucially having come up through theater school and L.A.)
so. she walks shane through his self-actualizing Big Gay Moment, discovers he's a LOT more like miles than she thought (that hole versus peg comment? oh, this man is desperate to gossip about his sex life), and decides she's going to keep him the way she and miles kept each other years ago. because fuck it. if she can't find a real boyfriend, the least the universe can do is deliver her another real friend.
