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I can’t tell if my boss wants to date me or if she’s just flirty

A waiter wonders about his manager’s intentions and if it’s even “cool” to date the boss.

Globe Staff

Need relationship advice? Submit your questions for Meredith here.

Q. I work as a waiter at an enormous entertainment complex in the area and have started a friendly albeit flirtatious relationship with one of my female managers who is easily 10 years my junior. We laugh, talk, work, and tease each other during our shared shifts, but I can’t tell if she’s genuinely interested in pursuing a relationship or if it’s all just innocent flirting.

Every time we work together and chat, she always says, “anytime you’re ready. . . . ”

Yesterday, after some of this same teasing, I asked her for her telephone number but she just giggled and dismissed me.


In addition to the age difference, there’s a racial difference. I know that shouldn’t matter but I’m wondering if that’s one of the reasons she didn’t give me her number. Or is it just that dating the boss is just not cool?

– Interested

A. Dating your boss is, in fact, not cool! You asked for her number, she laughed, so now it’s time to leave it alone.

I can’t tell you why she dismissed your request. I would guess it’s the work relationship, but it might be something else. Does it matter, though? You got a better sense of her boundaries. Friendly conversation is fine. Making moves for a real date results in a laugh. The flirting falls somewhere in between, and it’s confusing, so . . . don’t test it.

Some people will tell you it’s never good to pursue romance at work. I’d say there are great couples who met at work. They followed rules about disclosure and made sure they took the relationship out of the office. If one of them was the boss of the other, they asked for that to change.


You like this woman, but you don’t sound head over heels for her. It also sounds like you don’t know her very well. There are other people worthy of crushes. Shift gears and find them.

– Meredith


People act flirty and friendly to pass the time. Once out of the cage of work, reality checks back in. And who knows, maybe you actually are a funny, good-looking guy, and she is laughing at you not because she is flirting, but because you are cool to be around. Did you ever think of that? CEERINE

The “anytime you’re ready” remarks from the boss aren’t cool. She’s out of line and this sounds like a game to her, at the letter writer’s expense. MIDGE-

I just finished reading the letter, Meredith’s advice, and all of the comments. I realized that there’s an important detail that everyone overlooked. She’s your boss, which means that she has your number. If she wanted to date you, she would have called you. I think that you have no choice but to chalk this up to experience. Your takeaway should be that it’s not cool to play where you earn your pay. ADAM-NO-SPACE

It’s just flirting to make the shift go by faster. . . . This existed when I worked in a restaurant or two, in the Mesozoic Era. You asked for her number, she laughed, she dismissed you. Don’t analyze this for age, race, sexual preference, etc. You can meet other women. Do it outside work and not just in restaurants or bars. If you are a successful waiter, chances are you can interact pretty well with people and are presentable. Be confident and a nice guy. JIVEDIVA


Find the latest season of the Love Letters podcast at loveletters.show. Meredith Goldstein wants your letters! Send your relationship quandaries and questions to loveletters@globe.com. Columns and responses are edited and reprinted from boston.com/loveletters.