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I am a hormonal young woman and was craving an easy hookup, so I tempted fate (and horny dudes) on the Internet. Fate (and the dudes) took the bait, and of the hundreds of responses I received, one stood out because he accidentally attached a professional summary. I found out it was a man who works in my field, and is a fair number of years my senior. We met up; we hooked up; we became friends. He and I are both unmarried and unattached, but neither of us wants to have a romantic relationship with each other. I have now begun to date closer to my age group, so I don’t want to share playtime with him anymore, but haven’t told him yet. Being entry-level in the field, I could really use a mentor and have excellent access to this guy. I really don’t want to exploit him or make him feel rejected or awkward, and I want to be as professional as possible to keep suspicions of “secret lovers” at bay. Two questions: 1) Is it OK to pursue his help with my career, maybe in a formal informational interview or by asking for introductions? And 2) How do I go about this tactfully? Connect with him on LinkedIn and send a formal email to his work address? — Babe in Bossland
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 protected].