Help me get out of this weird friendship!
March 25, 2009 8:04 PM Subscribe
How do I politely and professional break of ties with a sort of creepy former colleague?
I'm a mid-20s woman. While at my previous company, I became "friends" with a relatively high-level guy at a client I was working with. It started when he indicated how impressed he was with my work, and we'd occasionally trade friendly professional email. It then started going down the path of politely teasing me, then occasionally into things like "I can't believe you don't have a boyfriend!" This guy has kids my age and (seems to be) happily married, so it understandably made me uncomfortable. But, for harmony between his company and mine, and also because I don't like dealing with this sort of conflict, I mostly laughed it off and talked my way out of uncomfortable moments.
Last summer, I noticed him acting very similarly with his young female intern, so this seems to be a thing for him.
Anyway, I left my old company, and over the last six or so months he's continued to email me with updates on what his kids are up to, or pictures from his family vacation, or sending me links he thinks I'd like. I've pretty much ignored them or just responded with a one-line "thanks, looks cool."
He's often self-deprecating, and if he says something that even *he* thinks could be construed as obviously inappropriate, he'll backpedal and say, "Just let me know if this bothers you." That puts me in an awkward situation, and I've never really been able to say "Yeah, this bothers me." I've only called him on something he said once, but that was because it was relatively public and other colleagues could REALLY have taken it badly.
Today I got an email from him asking "What's up? I haven't heard from you in a while. Should I stop trying to chat with you?"
How do I take advantage of this and finally bow out of this weird creepy "friendship" for once and for all? I want to be polite about it, because it's not unlikely that we'd run in to each other in professional situations in the future, and we have a number of mutual friends and acquaintances at my old company. But just as I haven't found a good way to do it in the past, I'm having trouble thinking of the right thing to say now.