The Hook Up: Bi and Bye



Dear Anna, I have always known I’m bisexual, with a slight preference for girls. I’ve been called out on this repeatedly throughout my teen years, but I’ve never openly confirmed or denied it. In high school, I made out with a few guys, and felt quite dispassionate about it. However, the summer after high school I entered into a longterm relationship with a guy. A month ago, we broke up after two and a half years.

Since we broke up, I’ve hooked up with a few guys, and I enjoyed those hook ups. The other night I went out with my manager from work (I work as an assistant in the bookstore, she’s the lower level manager), and we ended up making out. She also just got out of a longterm relationship with a guy. We saw each other at work after that night but didn’t talk about it. We’ve texted every day though, and she just changed her whatsapp image to a quote: “If you think about something at least once a day, don’t give up on it.”

I’m not certain what I should do. On the one hand, I’m awkward about pursuing a girl because I’m not totally comfortable with being openly bisexual. I’m also not totally certain of where she lies on the sexuality spectrum. And complicating all this is the little matter of us working together, and her being my direct superior! But I do like her. I guess. Do I like her enough to go through all this hassle though? What do I do? — Long Winded

Anna says: You do like her, you guess? That’s not exactly an enthusiastic endorsement, LW. And it sounds like you’re both in a heartbreaky place where you probably shouldn’t be pursuing anything “serious.” However, if you want to have the occasional make-out session or rebound with this gal … then, well, it’s still not the greatest idea because she’s your supervisor, but it’s a bookstore, not, like, some corporate law office or other rules-based establishment with strict dating policies. So it’s probably not going to ruin your career if you have a fling with your manager, in other words.

I’d invite this gal out for drinks with you again, and find out more about where she’s at. Tell her you enjoyed the making out and that you’d like to do that again, if she’s down for a low-commitment, casual, fun arrangement. If she’s not, oh well—no harm, no foul. Then you can focus your energies on other babely rebounds (or you know, on overcoming your heartache).

One other thing: Try not to parse her social media accounts in order to determine if quotes/song lyrics/cryptic status updates mean anything. I know it’s tempting (and Lawd knows I have done it myself too many times), but you’ll drive yourself crazy, so try not to.



Good evening. I have a question that I need an answer for since me and my friends were arguing about it. The question is: Can a relationship with a married woman (she’s married to a guy) with four kids work? It’s a hidden relationship. Is there a future to it? I think not, but my friends said it can work. If so, please tell me how? I think it would be so confusing, plus it’s hidden and there are many people involved. Am I wrong when I said it’s not going to work? — Jane

Anna says: And a good ‘morrow to you, Jane. Relationships that start out as affairs rarely work out. This isn’t to say it’s completely impossible (a few celebrity examples include Antonio Banderas and Melanie Griffith, Sting and Trudie Styler, and Prince Charles and Camilla Parker-Bowles), but starting a relationship as an affair heavily stacks the odds against you for a few reasons: One, it’s “hidden,” as you put it, and so your friend is forced to lie and be deceptive (and so is her married lady) in order to maintain it. This is emotionally taxing and tends to lead to a lot of guilt and other negative feelings. Two, she’s got four kids to think about. If the married lady were to leave her husband, could your friend take care of and support four children? That’s a lot to take on. Also, the affair might be used as evidence that she’s an “unfit” mother in a custody battle if her husband were to go that route. Three, there’s a tremendous amount of social stigma attached to affair partners (not to mention lesbian affair partners). If the relationship were to progress beyond its affair status, they would no doubt have to face the repercussions of it from friends, family, the ex-husband, and others, which many people have trouble dealing with. Four, because the relationship started out illicitly, the new relationship is likely to suffer from trust issues, i.e. “if she cheated with you, what’s to stop her from cheating on you.”

Shorter answer: You are right. You have my permission to try to talk your friend out of her affair, but, as we’ve talked about before, she probably won’t listen.

More you may like