Here’s a recent letter from a Dear Prudence column I thought you might find interesting:
Read Prudie’s advice here. My advice would be: Hell, no. Sure, knowing someone personally goes a long way when it comes to climbing the corporate ladder, but you don’t know this guy personally; you know him intimately. Whether you think you’ve become friends or not, chances are unlikely he thinks of you as anything other than… well, a plaything. He almost certainly has not thought of you in the frame of a professional colleague, potential career contact, or mentee. And asking for a “formal informational interview” isn’t going to change that. If anything, it will make him feel exploited, considering that you’ve now moved on to “someone your own age.” Oh, and when you do break the news to your hookup buddy that you’ve moved on, I’d refrain from mentioning age as your reason (no one likes to be reminded that he’s old). Instead, say something along the lines of: “Hey, this has been fun, but I’ve recently met someone I think has longterm relationship potential. I hope we can remain friends, especially if our career paths cross.”
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If you have a relationship/dating question I can help answer, you can send me your letters at email@example.com.