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