Is my older boss interested in me?

Dear Guys,

I’m 18 and my boss is 20 years my senior. He’s super attractive and single, funny and nice. He says things to me that could potentially be suggestive but I can’t really tell. He smiles all the time when talking to me, jokes around, and makes gentle fun of me. I truly can’t tell if he’s flirting, because I notice he doesn’t quite treat the other employees how he treats me. But he’s also in his late 30’s, so I’m not sure he’d even be interested.

I guess my question is, would you guys consider an 18-year-old if you were in his position?

Working Chick

Dear Working Chick,

Depends on what you mean by consider. He’s single, you’re of legal age, he’s clearly attracted to you and flirting with you—yes, those are all signs of flirting—so yes, he is interested in you, and considering you, but very likely he’s conflicted. First of all he’s not sure if you’d even be open to it. You are only 18, and he is 38. That’s quite a swing at your stage in life. Second, he is your boss. We don’t know where you work, but in most places of employment there are very strict boundaries between a boss and subordinate. Sure, work flings happen, but factoring in the age difference, he’d have to think very hard before crossing that line.

That said, he definitely is acting like a man who is interested in a woman, but we doubt he’s interested in anything other than a fun fling.

Our advice would be to keep your “relationship” right where it is, or even dial it back and return to a strictly professional arrangement. If you don’t, we believe this is not going to end well.

Take care,


ps. We hope you’ll let your friends know about us. Thanks.

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