Is dating the boss not cool?

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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 telephone number.

Or is it just that dating the boss is just not cool?

– Interested

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. Taking next steps gets you a laugh. The flirty falls somewhere in between and is 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 flirt with 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

Readers? Is the flirting really flirting? What should the LW do?