The Hook Up: 1-19-2012


I’m stuck in a tricky situation and I feel like I need an unbiased opinion and I also feel like I can’t trust my own feelings anymore. OK, I guess the best way to describe my problem is that I’m in a complicated half-relationship and I don’t really know what to do about it.

Just so you have a little background information, I’ll tell you that I’ll be 21 in two weeks and she is 33. We met about a year ago at work, where I became embarrassingly smitten with her. It was bad; I couldn’t shut up or stop smiling whenever she was around. She is hot, incredibly smart, funny, and taken as it turns out. When I found out that she was bi but has a boyfriend and two sons I never thought anything would happen. One night, though, a bunch of girls from work went out and we started drinking. I got brave and told her I liked her and we made out the rest of the night.

Over the past year we have spent a lot of time together and gotten really close. We’ve hooked up a few times (her boyfriend knows and is fine with it), and I lost my virginity in a threesome with her and her boyfriend. My initial crush has developed into more. I actually told her I loved her a couple weeks ago and she said, “That’s awesome. You’re my closest friend.” That seems pretty clear, but she sends mixed signals. In the past she has told me that she was interested and that she would probably get jealous if I started dating anyone. After I told her I loved her she said it would be selfish of her to keep me around and think that she could be what I wanted in a relationship, and in the same breath said that maybe she could and that would be an ideal situation. Then someone walked in the room and we haven’t talked about it since. I’m too nervous to bring it up again.

Does it sound like she might be interested in being polyamorous with me and her boyfriend? Does this sound like a relationship that is work pursuing? My head and my heart are totally conflicted. I would appreciate any insight into what she might be feeling or thinking.

Anna says: First, a housekeeping note! I’ve gotten a few emails recently about where to send questions. The answer is:, which is located in my bio at the end of every column. Just wanted to clear that up before we get down to biznass.

OK. Now, I think the better question is, do you want to be in a polyamorous relationship with this gal and her boyfriend? Would you be happy in such an arrangement? And by happy, I mean scream-it-from-the-rooftops, dance-like-no-one’s-posting-it-on-YouTube happy. The kind of unmitigated joy that advertisers try to sell to us in jewelry commercials but fail because Mock-Surprise Face is not the same thing as bliss.

I say this because I’ve been in your shoes before. There was a gal I developed a huge, melty crush on a few years ago. But she also had a fella, and the condition was that I had to share her with him. Most of the time this was fine because he lived far away, and I was nearby. We even had a threesome once when he came to visit. I should also say this was my first foray into polyamory. I’d had glimpses of it before, but there were no Big Feelings involved with any of my partners. Basically, what I was experiencing was low-grade polysluttery. Anyway. Eventually, my crush morphed into a full-blown love tirade, which was right around the time I realized that no, in fact, I did not want to share her. We started fighting about it, and I could offer her no better explanation than the simple fact that I had changed my mind. Half her heart wasn’t enough, and it never would be for me, so I pulled a Kelly on 90210 and chose me.

Of course, you’re not me, and this isn’t meant to deter you from going forth and prospering in this potential triad with your kinda-sorta lady. But I would certainly take heed when she says, “Awesome” in response to your professions of ardor, which sounds like a bro-tastic version of “Gee, thanks” if ever I heard one. If she had high-fived you afterward, I wouldn’t have been surprised. I would listen when she uses words like “selfish,” and I would listen to your own nervousness at the possibility of bringing it up again. The power balance is seriously askew here, which is further complicated by the decade between you in age. Not to mention the fact that you work together, which adds another level of clusterf—ery to the situation.

So again, I would ask yourself: “What would make me happy?” Is your love for this girl enough to offset the other, less than ideal factors that make up this scenario? I can tell you with some certainty that the odds are firmly against you. You’re going to end up getting hurt, if you’re not halfway there already. This isn’t to say that your girl will walk away unscathed, but you have more to lose here and she knows it. That said, I’m never one to talk anyone out of bold, impulsive decisions for love, especially while so young, so if you think you can weather this storm, then I say give it a shot. Ask her directly: Be with both of us. If she balks or makes excuses though, then you have to start weaning yourself off her. You have to direct your affections elsewhere. If you’ll excuse this impossibly cheesy simile, love is like a boomerang. If you throw it out there and it doesn’t come back to you, it’s not love. It’s a Frisbee, which is another metaphor entirely.

Here’s hoping yours comes back to you.

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