Q:

For years I’ve been wishing I could meet someone organically, off the apps, and now that that’s happened I have no idea what I’m doing! I recently met this amazing queer woman through a queer hiking meetup and we’ve hit it off — she’s incredibly talented and creative and kind, and we have some inside jokes going and have expressed we look forward to seeing each other on the hikes. We’re going to be hanging out one on one soon (I asked if she’d want to hang out, so not a date), and I want to take things slow so as to not freak her out and also, like, get to know her…but I also want her to get the the hint that I would like my face on her face.

My dating experience is pretty far and few between. I’m 27, and the longest relationship I’ve had lasted two months (we met on Hinge) and otherwise I’ve just pined after friends or been lead on in situationships that end abruptly once I express a desire to define things. How can I approach this new situation differently? I’m so excited, and either way will be happy to have made a new friend, but ugh I really don’t want to have to go back on the apps to find love!!

A:

Congrats on putting yourself out there and meeting someone you’ve hit it off with! “Queer hiking meetup” is exactly the kind of thing I recommend to people who are looking to meet people organically rather than the apps. You did it! Yay!

Now, I’m going to give you a little bit of tough love. Some of the things you say are kind of at odds with each other! You asked her to “hang out” rather than on a date so as not to freak her out, but you also want her to get the hint that you wanna kiss! I think you should be more upfront about what you want here. Asking someone just to hang out rather than asking them on a date when really what you want is to kiss could send mixed signals. On top of that, it might not even be clear to her that asking to hang out is different than asking her out on a date. It’s possible these things are distinct in your mind but less distinct in hers. This is what can often lead to the Am I On A Date conundrum some queer folks experience, a conundrum I think is best to avoid in instances where you’re genuinely interested in someone!

I know you say you’d be fine with friendship, but asking her out on a date or being more explicit about your intentions of getting to know her in a romantic way doesn’t make that possibility dead in the water. I think you might be striving for casual but instead landing on confusing. Not intentionally, of course! And there’s nothing bad about your approach, but you might set yourself up for success more if you are more clear in what you want here.

I do think there’s a clear explanation for your behavior here: your history of past situationships that end once you want to define things. But the thing is: You did nothing wrong or bad by expressing a desire to define things. That isn’t actually why the situationships ended. The situationships ended because the other person didn’t want the same thing, not because you asked for it. I know this can be a difficult one to ingest. But if you had held that desire in instead of expressing it, it only would have made you miserable and also prolonged the inevitable. You actually did the brave and healthy thing for yourself by saying what you wanted, even if it didn’t inevitably result in what you wanted.

You know you want to kiss her. You want her take the hint that you want to kiss her. So why beat around the bush with these hazy distinctions between “hanging out” and “going on a date”? You don’t have to be afraid of this ruining the possibility of just a friendship with her. I know so many people who have built really solid friendships with people where one person asked the other on a date and the other person said no or also when two people have even gone on a date or two before deciding to be friends. Being more explicit about asking her on a date doesn’t kill all other options for connection.

You get along! You have inside jokes! You look forward to seeing each other! You’re both queer! I don’t think you’re going to freak her out by asking her out. As for some brief flirting tips: simple compliments go a long way, but so does just listening to someone, asking them questions about themselves, and making eye contact. I mean, if you’ve already got inside jokes, flirting with her should be a smooth next step. Good luck, and have fun!

You can chime in with your advice in the comments and submit your own questions any time.

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