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Dear Quota Team,

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I sell insurance for a small company (22 employees total). This is my first job out of college and I've been here for 6 months. My sales manager has been incredibly helpful. He took me under his wing and taught me the CRM, introduced me to key clients, and genuinely helped me succeed in my first sales role. The problem is, he seems to think we're best friends now.

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He constantly asks me to hang out after work. He invites me to the bar to 'watch the game' and texts me about random stuff on weekends. The guy is in his late 30s, single, and lives alone. He knows everything about my girlfriend, my weekend plans, and even asked to join us at a concert last month (I got out of it when I told him he wouldn't be able to get a ticket next to us).

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I feel bad because he's been so supportive, and in a company this small, I can't really avoid him. I just don't want to be his social outlet. When I make excuses, he seems hurt and has started making comments like 'I guess you're too cool to hang out with your old manager now.'

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I'm worried that rejecting his friendship will hurt my career, but I also don't want to fake a friendship I don't feel. How do I handle this without damaging our professional relationship or making things weird in such a small office?"

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Reluctant in Location Withheld 

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Dear Reluctant,

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Don't make excuses about being busy, that implies you might hang out if your schedule cleared up. Set gentle but firm boundaries now before this gets worse. You can be honest and just tell him you like to keep your work and personal life separate. If he pushes back or gets hurt, remember that managing his feelings isn't your job. A good manager should respect professional boundaries, and your career shouldn't depend on his social life. Good luck!