She’s hot, cool, and dates women. Do I have a shot?

MrOswald asks: 

So this girl that I’ve been “talking to” lately was with a girl for two years until recently. At first I mentally marked her as a lesbian- no chance of getting with her. But she seems to be flirting with me. I’ve asked two mutual friends what her preferred sex is and they both basically said that they have no fucking clue what sex or species this girl is into and cite her most recent relationship and her high school rugby stories. She’s off an off the wall, hippie, med student, who is easily a 9 in hotness and is extremely cool… Almost too cool.

So, basically I don’t know if she’s talking to me as a soft-spoken bro or as a potential mate. If I mention the fact that I would like to date the shit out of her and she’s into girls, it could ruin a pretty cool friendship and I would look like an idiot.

I’ve thought about pointing out a good-looking girl and being like “What do you think about her?” But if she is into me, I’d look like a complete tool. I’m not sure what the hell to do about this… If anybody has any suggestion as to how to passively reveal her sexual orientation, I’d appreciate it.

Demetrius says:

Listen, I get that there are a lot of variables in the mix so I’ll try to address them all. Between her being “Cool” and extremely attractive and your fears around coming off as an idiot, I think you might be complicating the situation a bit more than you need to. Here’s what the situation actually is, versus how you’ve complicated it

The situation: You are attracted to a girl and you’re not sure if she is attracted to you

How you’ve complicated it: You’re attracted to a girl who dates women and also potentially men. You consider her to be very attractive. She’s cool, almost too cool (No clue what that means). If you ask her out you think it could ruin your friendship. You’re trying to figure out a passive way to see if she’s interested in you/interested in dating men.

Let’s cut through all the fluff for a second. You are attracted to this girl. She might be attracted to you. Ask her out. The End. You’re needlessly complicating a pretty simple situation. If she dates women but you think she might be interested in you, ask her out. The fact that no one is sure of her sexual orientation or preferences says to me that she’s subscribes to the belief of a sexual orientation scale and not a sexual orientation that is binary. She sounds awesome and if she’s flirting with you and you like her, how can she be “almost too cool” ? Everything beyond the basics of the situation is just fluff. All that matters is your attraction to her, and your belief that she might be attracted to you. Oh and trust me, if your friendship can be ruined by asking someone if they are attracted to you, it probably wasn’t that strong of a friendship to begin with. If you have a pretty cool friendship and she’s extremely cool as you put it, she’ll say Yes if she’s interested in a date or tell you No if she isn’t interested. I doubt she’d suddenly cut off the friendship because you tell her you’re attracted to her. If you’re that concerned with losing her as a friend, if she rejects you don’t talk about it after that. Just continue to do the same things you were doing before then. If you don’t change on your end and avoid complaining about being rejected, she’ll have no reason to change on her end.

Finally, don’t do the whole passive thing where you indirectly try to figure out if she’s into you, into men, or only into women. It’s pretty clear that she digs ladies, but she could also dig you. They aren’t mutually exclusive and it doesn’t have to be one or the other. Don’t ask her what her orientation is, because it doesn’t matter. Ask her if she’s into you. Be Direct.

Don’t complicate this situation by getting in your own head, or passively asking her if she likes you. If you like someone, ask them out, and deal with things from there.

Good Luck Out There.


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