The Hook Up: Am I leading her on?

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So, I’ve liked this girl for quite a while now—I’m talking years—but I’ve never said anything to her or made a move, because she happens to be my sister’s best friend and six years younger than me. She’s gay, she’s out, she’s been with other girls. I’ve been living in a different town for two years and I used to see her during the holidays, but a month ago I moved back to my hometown for work and I saw the opportunity of spending more time with her. We get on very well and we text regularly. I have a very good relationship with my sister but she is not OK with me liking her best friend. Not because she’s a girl, but because she’s very jealous and protective of all her friends. I was planning on having a serious talk with her to try to make her understand and once I did that I was going to confess my feelings to the girl in question.

But just yesterday, my sister told me that her friend had hooked up with this other girl who’s a friend of a friend. I started to cry immediately, inconsolably, like I hadn’t cried in years. At first she tried to console me, but then she said that she doesn’t understand why I like her. As if feelings were a rational thing.

So now I don’t know what to do. I lost someone in the past because I didn’t confess my feelings, and then I found out she would’ve gone out with me but by the time she found out, she was already too attached to the other person. I don’t want that to happen again, but I also don’t know if I should just blurt out an “I like you!” because I’m “in a hurry” and put her between a rock and a hard place. Should I confess my feelings before they go any further (I know they haven’t slept together yet, they only kissed one day) or should I step aside? If I did that I think it would be out of fear of rejection. Should I just go out on a limb?

Anna says: Girl, yes. Ask her out. One kiss does not make someone unavailable. One kiss doesn’t have to mean anything, except one pair of lips meeting another. It doesn’t signal DOOM to all future lips your crush’s might one day meet.

However, I also have to say I’m a little concerned about you, darlin’. You’re sobbing inconsolably over a girl who is single and can, ostensibly, do whatever she wants. This isn’t to invalidate your feelings, by any means, but that kind of a reaction makes me think there’s something deeper and unresolved at stake. Perhaps it’s a feeling of missing out, or another reminder of the experience you had where you kept your feelings to yourself and regretted that decision. Perhaps it’s something else altogether, but I encourage you to turn the microscope on yourself for a moment and see if something else is there besides that kiss.

But also, girl, yes! Ask her out. Go out on that limb. Go go go. “Gather ye rosebuds while ye may” and all that. If you continue to use waiting as the main tactic in your romantic relationships with women, you’re going to inhibit yourself and your future potential lovers, and your fears will only widen. It’s sweet that you were trying to accommodate your sister’s needs, but really it has nothing to do with her. It’s between you and your crush.

And just to clarify, you wouldn’t be confessing your feelings because you’re “in a hurry.” You’d be confessing your feelings because they are true and real and big. I think at this point, sugar shoes, the fears of regret should outweigh the fears of rejection. You’ve been down that road before. It’s time to take another path and see where that leads. Regardless of your crush’s decision, the step you make will be good for you (though I surely hope she reciprocates those Big Feelings). Withholding has made this crush bigger than it needs to be. It’s time to figure out where she stands. It’s time to give yourself a shot.

So do it. Be brave. Be authentic. Your life and happiness depend on your willingness to make calculated risks in the direction of love. Everything else is secondary.

Now go. We’re rooting for you.

For years, I’ve wanted nothing more than for a girl to really like me. I’ve tried “dating” many queer girls who were never sure what they wanted, who led me on, lied to me about their feelings, hurt me and ended things after a few weeks at most. I’ve never had a real relationship, but I’ve always been ready for one. Now I’ve finally found a girl who likes me a lot, but I can’t figure out how I feel.

She was a teammate of mine who I had a little crush on for a while, but gave up on it when I learned she was straight. When the season ended she confessed that she was attracted to me, and we’ve been hanging out and hooking up for a few weeks now. Even though she’s never liked any girl before me and was a little freaked out about everything at first, she is taking it all completely in stride. She told her best friend about us and plans to tell her parents soon too.

She’s always telling me how much she likes me and how she could never like any other girl, but I just haven’t been able to bring myself to reciprocate. I don’t know why. I like her a lot and all our friends say how good we are together. Maybe it’s partially because I’ve never been friends with someone first before hooking up. I just can’t figure out how I feel about her. I want to keep seeing her and just see where things go, but I don’t want to be the asshole who leads her on like everyone else has done to me, especially with her first girl experience. We’re probably going to be teammates again in the future.

I do like her and enjoy being with her, but for some reason I just feel very blasé about the whole thing. What should I do?

Anna says: You don’t have to “do” anything, per se, except pay attention. And to be as upfront as you can. It’s OK to be uncertain, or to “enjoy being with her” and also feel blasé. It’s not leading someone on if you look inside yourself and see a genuine question mark. That’s dating. It’s figuring things out. It’s learning about one another and sharing and growing until one or both of you determine that it can’t go any further.

While you are muddling through your feelings, I would tell your lady about your uncertainty. It might not have anything to do with her actually. You can tell her what you told me in your letter, though I’d probably avoid the word “blasé” in your explanation. It might simply be that the two of you work for a little while in limited ways and that was that. I think perhaps your past experiences have colored your views. While it’s upsetting that your past lovers have lied to you about their feelings or otherwise, to “lead someone on” is a deliberate and malicious act, usually involving a degree of manipulation. What you are doing is not that. So you can carry on with a clean conscience.

That said, if and when those feelings form less ambiguous punctuation in your mind, then you have an obligation to tell her what the question mark has become (hopefully not an emoticon). If it doesn’t work out, then that’s OK too. In fact, I’d say it’s a good sign because it proves that even though you “really want a relationship,” you’re not willing to fake it. It means you’re willing to be alone if it means being true to yourself and feelings. This is her first girl experience, yes, but first or hundredth, it’s the same—we all want to be treated with humanity and kindness. You are only responsible for you and your actions. There’s no need to speculate how your relationship now might affect your lady’s relationships in the future.

A word of caution, however. If, after a few more weeks or maybe months, it becomes obvious to you that her feelings are way disproportionate to your own, and there’s very little chance yours will change, then end it sooner than later. Those kinds of glaring power imbalances never lead anywhere good, in my opinion.

But, again, there’s no rush.

It’s been a few weeks. Get to know her. Find out if you click. Sometimes the slow burn of a friendship-turned-relationship is far preferable to the ones that burn hot and fast and fizzle just as quickly. Sometimes it takes a minute to transition from friends to something more. Keep showing up and keep paying attention and you’ll be aces.

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at annapulley.com and on Twitter @annapulley. Send her your The Hook Up questions at askthehookup@gmail.com.   

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