On a roller coaster with my boss

Dear Meredith,

I'm a 29-year-old queer woman and made the mistake of falling in love with my boss, "Jane." She owns the company where I work. Jane was separated from her partner at the time.

When we first got together, I told her that I would forget it and that things could go back to normal. But she promised, promised, promised that she and her partner weren't getting back together, and inside I was thrilled. So we started dating. We were pretty out in the open about things. Everything was great for about a year and a half. We were even talking about moving in together. Then she told me her partner wanted to try to get together again and work things out, in part because she has a child who was really upset by the split.

I wanted to do the adult thing, so I said OK, but I would be lying if I said I wasn't hurt. For the first couple of months, Jane was pretty frosty around me. She can be pretty critical at times. She says she's only sharp with me to make me better at my job. She told me it was hard for her to work with me because I take the things she says too personally. I began discreetly looking around for a new job and knew I could probably move on, though I would lose some money if I did.

Then, last week, Jane and I had a drink and she told me she wanted to start dating again. She wanted to stay in her partner's life, but they decided they can't live together. Jane wants our relationship to go back to the way it was. She apologized for hurting me. If I'm being honest, I do love Jane. I feel wonderful when I am with her, and I do sometimes think we are soul mates. But part of me wonders whether this is really the end of the roller coaster, or if this is just the slow stretch pulling us up the hill for the next stomach-churning plunge. And if we broke up again I don't know if I could stand it. I'm just not sure what to do.

– Roller Coaster Girl


There are two issues here: Your romantic relationship with Jane and your experience at work. The work issue needs to be addressed no matter what. The minute you started dating, you should have been reporting to someone new.

Sure, she owns the place, but she should have acknowledged her conflict and made it known. You can tell her that you need an objective person to evaluate your work performance. It would make life easier for both of you.

Please know, by the way, that you're not being over-sensitive about anything. It's not easy to work with an ex, and it's even harder to be managed by one.

As for your romantic relationship with Jane, you'll have to go with your gut. Would the pain of another breakup be worse than the bad feelings you'd have if you passed up the opportunity to date a possible soul mate? That's the big question here.

You're allowed to take your time as you figure this out; Jane shouldn't demand immediate answers. When it comes to your personal life, she is not the boss of you.

– Meredith

Readers? Thoughts on all of this?