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Ahoy, Captain! Maybe this is a pleasant problem to have, but it’s a puzzling one.

I’ve been spending a lot of time lately with a woman I find very attractive, trying to figure out whether I want to ask her out or not. We have a lot of interests in common, and do plenty of things together, but have different interests too. (I like this for a couple of reasons – the fact that she’s not into knitting means that my knitting group will always give me space from her, for example, and on the other hand she’s introduced me to a fun new sport I never would have tried otherwise.) I find her fascinating and really easy to spend time with – she’s just a very friendly person. I really, really want to make out with her, and from the way she’s acted towards me, I think she’d be pretty open to the idea of taking this from friendship to dating.

I’ve been holding back from that step, though, mainly because I feel I need to know people a bit better than I know her before I go there. (I’ve never been attracted to someone this quickly before – it’s both exciting and a bit weird.) It was actually a comment on a recent CA post that made me wonder if I should reconsider it altogether. I can’t find the comment, but it said something along the lines of “People who won’t respect your boundaries will tell you through their actions – they’ll touch you without asking, they won’t notice when they’re interrupting or dominating the conversation, and they’ll tell you inappropriately personal things.” That pretty much describes my friendship with her so far.

There’s a lot of physical affection in our friendship, which I love, but it did start with her touching me without permission – I just didn’t care, because I liked it. When something’s bothering her, she does tend to steamroll over other people in conversation until she’s exhausted her need to vent. And we hadn’t gotten to know each other for very long before she hinted to me that she’d been abused and lost most of her friends over it, though she only recently told me all the details. But although I was sympathetic, even at the time I thought it was a big leap to even drop me hints about this stuff when we hadn’t known each other long.

Captain, I don’t know what to do here. I really feel for her over what she’s been through recently, having survived the same kind of abuse and subsequent loss of support network myself. I want to do what I can to support her through that, and it’s clear she still has a lot of feelings to work through. But I do worry about some of these things, especially the way it’s almost impossible to get in a word in with her when she’s upset about something. It seems like the sort of thing that should be a red flag, or at least a warning to be careful while I continue to support her. And yet, I really like her! She’s very attractive to me in all sorts of ways, I love being around her, and she gives me warm fuzzy feelings in a variety of body parts. I just worry that my happy feelings are drowning out warnings I should be listening to. Or maybe that I’m just a bit desperate – I’m a lesbian and it’s really hard to find queer girls I can talk to in my area.

How do I tell whether to ask her out or not when my logic-brain says to be cautious but the rest of me just wants her?

I’m going to answer a question with a question and then let the commenters have at it.

Is there some reason that you cannot casually date this woman?

As in, be friendly, enjoy what there is to be enjoyed (ahem), but don’t try to lock her down as the Love of Your Life?

You’re smart to pick up on some of the red-flaggy behavior that’s not what you want in a partner, and you’re smart to not let the pants-feelings cloud your judgment, and you’re generally smart to be cautious, but I think the script you’re looking for is:

Would it be okay if we made out sometime?

And when she’s dominating the conversation, the script is:

“Hey, I’m sorry you’re sad. Is it my turn to talk yet or is this more of a monologue situation?”

I know you’re trying to be a good citizen of Feelingstown, but you can’t control everything that will happen and everything that everyone will feel. Definitely not all pantsfeelings need to be acted on, but you’ll never be this young again and obviously you both want to. Sometimes that’s a good enough reason.

Okay. Enough of being the devil on your shoulder. If your gut really says to not get involved with this woman for some reason – she just reads like Trouble to you – then listen to it, and put a stop to the flirty-touching stuff. But there’s nothing wrong with wanting someone, and there’s nothing wrong with wanting someone who you don’t necessarily end up with in any kind of serious or permanent way.

Shameless Plug Alert: Our friends at King Is A Fink have a new webseries out. Watch the trailer here. The After Ellen reviewer called it “one of the most heartbreakingly authentic stories about LGBTQ youth I’ve ever seen. It is The Misfits meets Skins meets modern-day Dickens, if Dickens had grown up gay and gotten his hands on a video camera.” It’s up our collective alley, I think.

Dear Captain Awkward;

I have liked this girl for a while now, or at least we seem to have strong chemistry. Sometimes we hang out and there are these tense moments of “Are we gonna kiss?” that I think are on both sides. The caveat is that she is already dating someone (who sounds kind of sucky, at least in the dating capacity) and I don’t want to be romantic with her because of the aforementioned detail and also ’cause we’re functioning fine as friends.

So how can I reliably deal with attraction when I don’t want it? My current strategy is to think about how creepy it is if I think we have a spark and she doesn’t, but that doesn’t appease my annoyance with the situation for long. Also, I should probably never mention this whole thing to her, right? 

-Some Dude

Dear Some Dude:

Hang out with her less and explore other dating/romantic/crush opportunities for yourself and let the attraction subside naturally.

If she asks you why (and you do actually want to start something up with her), say “I’m pretty sure if we kept hanging out so much we were going to end up making out, and I don’t kiss girls who have boyfriends.

If you don’t want to start anything up with her, having chemistry with someone doesn’t mean you have to act on it. Chill out and enjoy the friendship (in smaller doses). Find someone else who welcomes your attention.

Thanks for giving me the excuse to post this video:

Fred Savage in The Princess Bride. "Is this a kissing book?"

“Is this a kissing book?”

Dear Captain Awkward,

I’m in love with my best friend. That sounds like a really lackluster problem, but it’s really starting to weigh on me in a way it never has before. I’ve tried to talk to some other friends about it, but they don’t really seem to count as outside opinions (our friends are basically gunning for us to get married). I would really appreciate an unbiased viewpoint!

My best friend is wonderful in every way. We’ve been inseparable since high school. Everything we do together just seems so special and memorable, like a movie. We can keep up with each other and encourage each other. We adventure together. We can talk to each other in a comfortable stream-of-consciousness and work out our problems together. We grew up together. It’s been five years and my heart still jumps up into my chest every time he walks through the door.

I’m so in love with him, but I’m starting to wonder if anything will ever change between us. If we ever started to date, physical intimacy would be the only new development; we’ve already covered most of the bases for beginning and sustaining a healthy relationship. I’ve reached a level of intimacy with him that I’ve never found with anyone else. Pursuing a relationship with him seems so strange to me. It’s something I thought about a lot when we were a bit younger, but now it just seems silly. I see us staying friends forever, and I could even picture us being married, but I could never see us in a relationship together. It’s just been too long- it almost seems like we’ve passed the mark. I just don’t see anything to be gained by dating each other.

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