I’m a mid to late 20s fresh attorney. I work and network in a new city. Got to know one my law firm boss’s friend (also an attorney in his early 40s but in a different practice) who is a lot friendly to me? He asks me out to lunch and texts me personally. I get we are all adults here and it’s an off leash ball park, but it also feels weird.

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If you’re uncomfortable with it, then set boundaries. Keep conversations brief. Don’t entertain lunches. Keep any conversations strictly professional. A man in his early 40s chasing 20-year-olds does so because women his own age don’t want him. Don’t entertain man-children. Know your worth and trust your instincts. If it feels off, it’s because it is.

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Thank you. Unfortunately, it’s borne out of personal experience.

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Sorry you’re in this position. I would keep it strictly professional and stop responding to anything past that. He’ll get the hint. The piece where it’s your bosses friend makes it creepier.

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