Love Letters

Surviving at work, after dating the boss

Her boss broke up with her, and the office got frosty. Should she let things heat up again?

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Q. Dear Meredith,

I’m a 29-year-old queer woman and made the mistake of falling in love with my boss, “Jane,” who owns the company where I work. Jane was separated from her partner when we got together, and promised they weren’t getting back together. Inside, I was thrilled. Everything was great for about a year and a half, and we talked about moving in together. Then her partner wanted to try again, in part because her child 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 critical, though 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.


Last week, Jane and I had a drink and she told me she wanted to start dating me again. She and her partner decided they can’t live together. Jane apologized for hurting me. If I’m being honest, I do love Jane. I feel wonderful when I am with her, and sometimes think we are soul mates. But part of me wonders whether this is just the slow stretch pulling the roller coaster up the hill for the next stomach-churning plunge. If we broke up again, I don’t know if I could stand it.

 — Roller Coaster Girl

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A. 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 started reporting to someone new. Sure, she owns the place, but she should have acknowledged her conflict and made it known. Tell her you need an objective person to evaluate your work performance. It would make life easier for both of you. Please know, by the way, you’re not being over-sensitive. It’s not easy to work with an ex, and 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?

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


I can’t imagine having to deal with relationship drama while at work. Work drama is exhausting enough. HAPPYDAZED


“Jane” has not taken any responsibility for her actions so her apology (months late) is insincere and meaningless. Is this really how you want to be treated by your soul mate?AULDYIN

Historically, I don’t think “second chance” relationships do so well. MCDIMMERSON

You’re the placeholder until the ex calls her again. Get a new job and don’t look back! CONCERNEDCITIZENONDUTY

Meredith Goldstein is in her eighth year writing Love Letters for the Boston Globe.

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