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 long-term 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 hookups. 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 long-term 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
Dear LW,
You do like her, you guess? That’s not exactly an enthusiastic endorsement. 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, a bookstore probably doesn’t have uber-strict dating policies in place. (Find out what they are, if any.) In any case, it’s probably not going to ruin your career if you have a fling with your manager.
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 (I have done it myself too many times), but you’ll drive yourself crazy, so don’t. Focus your energy on literally anything else. Learning Victorian slang for cunninlingus. Figure out why Epsom salts relieve sore muscles. What exactly is a black hole? (Actually, report back on all of these questions. Inquiring minds want to know.)
Dear Anna,
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? — J
Dear J,
Relationships that start out as affairs rarely turn into committed, healthy, long-term arrangements. This isn’t to say it’s impossible, but starting a relationship as an affair heavily stacks the odds against the couple for a few reasons: One, it’s “hidden,” as you put it, 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, resentment and other negativity. Two, she’s got FOUR kids to think about. If the married lady were to leave her husband, could she support herself and her children? Would your friend take care of and support her four children? That’s a lot to take on, even in the greatest of circumstances. Also, depending on what state she lives in, if it were to get out, the affair might be used as evidence that the married lady is an “unfit” mother in a custody battle. 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, the couple would no doubt have to face the repercussions of it from friends, family, the co-parent 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: It’s not impossible, but it’s unlikely to work out. You have my permission to try to talk your friend out of her affair, but, as I’ve said before, she probably won’t listen, because the heart is an a—hole.
