Dear Wendy
Dear Wendy

In Other Words: “Can I Ask My Hookup to Be My Career Mentor?”

Here’s a recent letter from a Dear Prudence column I thought you might find interesting:

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.”


You can follow me on Facebook here and sign up for my weekly newsletter here.

If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.

17 comments… add one
  • lets_be_honest August 1, 2013, 2:14 pm

    Oh God, WWS!

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  • theattack August 1, 2013, 2:18 pm

    Oh my…

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  • Lily in NYC August 1, 2013, 2:35 pm

    I’m not sure this is all that terrible depending on how you handle it (as long as he truly doesn’t have feelings for you). I helped a casual fling get a job at my newspaper (old job) and he ended up winning a Pulitzer Prize a couple of years ago (I pinky swear it’s true!).

    I wouldn’t explicitly ask for help or for him to introduce you to people, but I think it would be ok to ask for advice and then hope he offers more help. If there’s any chance he will expect you to continute fooling around with him in order to get his help, then stay away. I doubt this will work well but I don’t see the harm in a simple request for advice. But don’t send a formal email.

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    • Lily in NYC August 1, 2013, 2:36 pm

      Oh dang, I answered thinking OP might actually read the comments because I forgot this was from Prudie (who I think gives terrible and sometimes dangerous advice – she should not be an advice columnist).

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      • Alena August 1, 2013, 7:39 pm

        I don’t always agree with Prudie, but I don’t think I remember too many pieces of advice that I have been horribly appalled by.

        Now I’m curious, what advice does she give that you think is so terrible and dangerous? I’m truly curious, not trying to seem like a jerk. I know enough people dislike her advice that they have a facebook group dedicated to it.

      • KL August 2, 2013, 6:48 pm

        She had an awful column recently where her advice was bad because she didn’t understand technology. The post was about someone thinking her stepmother was cheating because her picture showed up in a dating ad–it was almost certainly Facebook’s ad software at fault, and not an affair.

    • Fabelle August 1, 2013, 2:41 pm

      Yeah, I don’t think it’s that terrible either. This is how everybody gets jobs nowadays, right? (Shh, I’m kidding!) But yeah, I dunno. It’s not that hard for him to pretend he knows her from somewhere else, if he did decide to help her along.

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    • ele4phant August 1, 2013, 4:10 pm

      I agree. It would be one thing to ask him to officially mentor her or ask him to connect her with any one, but after the affair has ended and time has passed, an informal email asking for a specific advice is not that terrible. Why not try? He could always ignore her email if he feels its weird or inaaproporiate. If he’s a decent enough guy, he should recognize that’s she’s a real person and not just a plaything, with aspirations in his field, and as long as there’s no bad blood why wouldn’t he be willing to help someone. Be her full time mentor or pave the way for her, no, but I can’t see why he would be unwilling to answer a short question in relation to their shared field.

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  • GatorGirl August 1, 2013, 2:38 pm

    No. The answer is no. Good grief. How would you have him introduce you to people

    “Paul, please meet Babe.”
    “Lovely to meet you Babe, how did you and Joe meet?”
    “Funny story actually, we used to be fuck buddies but I got bored. Now I just milk him for career hookups.”

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  • mylaray August 1, 2013, 2:50 pm

    Oh gosh, it’s a bad, bad idea.

    But I feel the need to share a similar story…when I was single, I met a man at a party and we quickly became friends. Though, not long after, we started hooking up. It didn’t take long for me to find out that his dad had a very, high-level executive position at a Fortune 500 company, one I had dreamed of interning/working for. I never once asked for anything, he volunteered on his own that he could get me an interview there when he found out that was a company I would love to work for. I said yes, and I ended up getting an internship there which got me to places I wouldn’t be today without that. We were never interested in each other romantically, but he was a great guy, and we hooked up for awhile because I was looking to have some fun. I didn’t intentionally use him and his connections, but it still made me feel bad at the time. We’re still friends (just friends!) years later, but I would never advise anyone to do anything similar, because it can end so badly, and I’m the type that likes to keep my work life separate from everything personal. It’s also something I don’t believe is right/fair to do intentionally.

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  • oldie August 1, 2013, 4:32 pm

    Doesn’t hurt to get a little informal guidance from him, based upon his career experience. Using him for references/introductions can backfire in a bad enough way to make you truly memorable to a lot of the hiring decision makers in your field. Btw, I really doubt he ‘accidentally’ attached his career summary. That was the “I gots the money’ come-on for a guy looking for a sugar baby. Luckily for him, he got you much more cheaply.

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    • oldie August 1, 2013, 4:35 pm

      Btw, bad title by Wendy. The question isn’t ‘can I hook-up with my career mentor?’ She wants to be done hooking up with him. The question is ‘can I turn my hookup buddy into a mentor’ or more precisely ‘Is it cool to tell him I don’t want to hookup anymore, but I’d really like him to mentor me and help out with my career’.

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      • Fabelle August 1, 2013, 4:37 pm

        Huh? but the title is “Can I Ask My Hookup to Be My Career Mentor?” That’s basically what the deal is, even though she’s kinda done with the dude.

  • muffy August 1, 2013, 4:35 pm

    It’s not terrible if you let enough time pass by – it’s not too different from an ex boyfriend say. I think it may be likely he would say no though or wouldn’t have much help to offer you anyways – I mean if he doesn’t want to date you chances are you guys don’t mesh well which means he probably isn’t going to help you out too much. I also don’t know how a current boyfriend would feel with you being career mentored by a person you had a sexual relationship with. But after some time maybe reach out and say hi in an informal email and ask if he has any career advice for some specific problem you’re experiencing in your field.

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  • lets_be_honest August 1, 2013, 4:57 pm

    Idk. Read everyone’s comments. If I were this guy, and went out looking for just a sex buddy, and then she decided she wanted to use me for more, I’d be annoyed and definitely not want to help her at all. Get ahead on your own. If he knows the field you’re in, and actually wants to help, then he’ll offer. I would have zero interest in helping my fuck buddy get ahead in my field.

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  • Lindsay August 1, 2013, 5:33 pm

    This seems like a bad idea. For one thing, it’s probably going to come across as though she’s using him. Especially if she does it right after dumping him. Plus, I think it’s just iffy to mix romance and work like this, especially in the form of a fuck buddy. There’s no guarantee that they aren’t going to act like an asshole (or spill the beans, at the least), and I think it would be kind of weird if someone figured out how they know each other. I also think that his view of her is likely framed by the whole sex thing and not who she is as a professional (or possibly even a person).

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  • Chiara August 2, 2013, 10:52 am

    I don’t think it’s as bad as it sounds – it all depends on how you approach it. I don’t think you should go full blown professional when reaching out to him for help because it might make it seem you’re uncomfortable. Personally, I’d reach out and be like, you know.. I’d love your help. Don’t think too much about it and start easing off the ‘other’ connection. He doesn’t want a romantic relationship and men are a lot more simple than we think. He’s not likely to sit an ponder on it that much and men have a general appreciation for showing their status by making introductions. I think the more nonchalant you are, the better.

    If your situation is as no-strings attached-ish as you claim, go for it!

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