My Newly Engaged Straight Best Friend Is Being Gay Towards Me

ok i need outside perspective because i’m losing it. my best friend is straight, or “straight.” last weekend at a bar in front of her fiance AND the girl i’m dating she said “honestly if you had a dick i’d leave him” (yes i know this is a cissexist view of sexuality) and everyone laughed and i laughed and then i went to the bathroom and stared at my hands for like 10 minutes.

this is not the first time. she has been doing this constantly for the last few months, i don’t know what triggered it but it feels linked to her getting engaged. “you’re my real soulmate.” “my therapist thinks our friendship is the healthiest relationship i have.” she compliments me all the time.

we used to be super physically affectionate and at one point lived together and slept in the same bed. (it was a small apartment.) that dialed back when she got this boyfriend who she is now engaged to, because he told her it was weird how touchy we were with each other. or that was just part of growing up. so a mix of both of those factors.

here’s the thing — i had a crush on her back then. i got over it. i moved on. i learned self-respect.

but every time she does this it’s like she knows exactly what she’s doing and also has no idea what she’s doing. do i say something? do i just say “hey can you stop” like a normal person? what if i don’t want her to stop? i feel like if i bring it up i’m the one making it weird when SHE is making it weird.

Valerie: I don’t think it’s making it weird to ask her to stop specifically talking about how she would date you if she could. You can explain that since you ARE queer and you’re dating someone, it’s a bad look to have your female best friend talking like that. I think in general compliments are normal – like “our therapist thinks our friendship is the healthiest relationship I have” is really sweet actually – and maybe your past feelings about her may be coloring those as a little more flirty than she means them to be. Platonic soulmates are real! But specifically talking about being IN love with you and wanting to date you and leaving her fiance for you etc, I can see those jokes being not okay and I think it’s perfectly acceptable for you to ask her to tone those down. At least in front of other people. You snuck in a little “what if I don’t want her to stop” and that feeling is something entirely separate you have to contend with within yourself. I think having this conversation with her and telling her that she can’t just say things like that she’s in love with you if she doesn’t mean it could open the door for you to ask if she DOES mean it, if that’s really somewhere you want to go. But that’s another question entirely. In general, I don’t think asking her to tone down the flirty sentiments is weird.

Summer: I’m not good at reading signals but even I can tell that she has a fascination for you that goes beyond a good friendship. The fact that her fascination has pushed her partner’s boundaries is also concerning because it means she didn’t reel them in naturally. She had to be told to reel them in or jeopardize a relationship. And evidently, she’s still doing it.

Your discomfort with this is pretty clear. This isn’t reciprocated. It’s impacting her relationship (possibly not your business) and it’s impacting your well-being (very your business). Yes, the ‘normal’ thing to do would be to sit her down and tell her it’s inappropriate and she needs to stop. That if what she says is genuine, she needs to cut it out unless her life is in a position where she can make those pursuits. And even then, you’re pointedly not interested. That’s easier said than done since her feelings might be genuine and she may take it harshly. Or she might try to deflect or brush it off and the can gets kicked down further?

I don’t enjoy bringing up worst-case scenarios so I’ll just tell you that… best friends come and go. And best friendships are allowed to end when the union has outgrown a person’s antics.

Ashni: Ugh, this is extremely weird and you should say something. Even something as simple as “Hey, I felt weird about you saying that you’d leave your boyfriend if I had a dick” could suffice. It’s just a wild statement to make in general, and in front of both of your partners too just feels disrespectful to all involved? I don’t think you’re making it weird at all, you’re expressing hurt and ideally, establishing a boundary in a relationship that can handle boundaries being set! If she loves you, she’ll respect the boundary. The longer you let it go on, the more she’ll think it’s an acceptable behavior to continue. I’d be experiencing such a complicated mix of emotions, though, if I were you, and I really am sorry. I hope she’s able to receive the feedback and change. Also, for what it’s worth, if you don’t want her to stop (to your point at the very end)? She’s still engaged to another person, and I can’t imagine hearing these things makes you feel good.

Nico: If I’m speculating, I would say she is doing this as an attempt to get and keep your attention. Maybe she even knows you used to have a crush on her. Or, alternatively, it could be from her grappling with some part of her sexuality that she isn’t fully aware of or willing to admit to but that she feels is potentially being pushed aside by her “straight” engagement. Finally, some people are just really touchy-feely or they’re really touchy-feely with people they feel comfortable around and she may not have any notion that this would make you in any way uncomfortable. Regardless of the reason, though, if it makes you uncomfortable, then as someone who values your friendship as much as she says she does, she would ideally look at your feedback about the situation and be happy to change her behavior. I also don’t think it’s weird to gently inquire into why she thinks she’s making these flirty comments, as long as you’re prepared for things to potentially get deep.

Riese: Okay it feels possible to me that you’re the one she has wanted all along and now that she’s closing in on actually marrying someone she’s starting to realize this, so it might be worth like a genuine, actual, honest conversation about where she’s at and how she feels.

After a really long string of relationships where I got my heart broken, I know now– I want something serious (a life partner, a companion, Love, a future). Where and how do I find that? The apps don’t seem to be the place, nor the club. What is the place? I’m so tired of casual!

Summer: Honestly, mood. Dating apps are a wasteland since they were enshittified. And clubs/bars cater to a certain kind of dating that might not match your needs or the demographic you want. I say that as a 31 year old who lives in a student town and has been hitting clubs again this year. It’s like a daycare out there.

Even though I don’t like apps, I still think they have potential because they let you filter out people who really don’t match your needs and take chances on people who might align with you. That’s better than proverbially throwing darts while blindfolded at a bar. But once your apps run dry in an area, it does get dire. I’d suggest to keep an eye on the apps and check occasionally, but not stake your hopes there.

I will instead lean back on the joy of shared activities that grownups do. I don’t know your age or where you are in life, but if you’ve had a ‘long string of relationships’ and are ready for a life partner, it sounds like you’ve outgrown the nightclub scene. Maybe consider taking up activities where queers might congregate (ren faire, group picnics, handicrafts) and just socialize. It’s best to not be the person who goes to a social gathering specifically looking to date. But if you enjoy the activity and make some friends, it’s still a better outcome than nothing. And who knows, something might come of it.

Ashni: Maybe a controversial take, but I think you’re already on your way to finding something serious. Your long string of relationships and heartbreak, while devastating (trust me, I’ve had my fair share), is a string that’ll eventually lead you to something serious. Every bad date and weird interaction at the club is just you weeding out people who aren’t right for you!

I’m … unfortunately a proponent of the apps. I know they’re terrible and trash and even the ones “designed to be deleted” just want you to shell out for premium memberships, but they also led to my last three serious relationships. One was a domestic partnership, another was more of a chaotic, intense thing that only two lesbians could create, and I met my current girlfriend courtesy of a dating app swipe. All this to say, the apps have led me to serious things so I wouldn’t discount them entirely!

Hard agree that the club’s not it, though. Is there a queer sports league in your town, or maybe a queer book club? Echoing Summer’s suggestion that putting yourself into the queer scene as much as possible is probably your best bet. If nothing else, you’ll gain new gay friends – and as a bonus, they might have hot gay friends they can introduce you to. No apps or club required, just old fashioned setups! Honestly, setups feel inherently more serious than a regular date anyway because you and your date both have to answer to the shared friend that made it happen. If I were you, I’d plant some seeds with queer friends to see if any of them might have single, queer friends they think you’d be a good match with.

Nico: Dating is, unfortunately, a numbers game. You need to keep putting yourself out there and having so-so to heartbreaking experiences until you find something that is working for you. I am actually also in favor of using apps for this reason. I do recommend liberally swiping left and being highly selective once you get on there. The algorithms respond to specificity better I’ve found. It makes me feel guilty to swipe left on people who maybe could work out but who don’t quite seem like who I’m looking for, but it yields better results in the long run because the apps remain evil tools that we pretty much have to use if we want to date. Besides apps or meeting through shared activities, I also know a queer couple who met through Tumblr, and I have definitely gone on dates after someone’s slid into my Instagram DM’s and chatted me up, so while also a hellscape, don’t discount looking at your social media connections if you use it. Take the time to say hello to people, to comment, to randomly send someone cute something you think they’ll like.

And in the meantime, nobody likes someone whose hobby is dating. Participating in in-person, adult activities that match your interests is a surefire way to meet new people and to help yourself glow with interesting anecdotes, self-esteem, and the power of friendship, all of which are highly attractive qualities. And while, like my colleagues, I recommend you find some interests-aligned queer meetups and activities to attend, I also recommend mixing things up between exclusively queer activities and activities where queers might be present. You’ll find some interesting yet elusive people working to keep your local trails debris-free or line-dancing or finding foster homes for senior dogs, or whatever calls to you. You never know, you could even meet a straight person who has a queer friend they will want to try and set you up with. No matter what, you cannot find love if you don’t take your chances.