Help! Can I Ask My Hookup Buddy to Be My Professional Mentor?

Advice on manners and morals.
July 25 2013 6:15 AM

Performance Review

I’ve been sleeping with an older man in my field. Can I ask him for career advice?

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.



Dear Prudence,
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 move 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


Dear Babe,


Dear Prudence: Not-So-Secret Life

Dear Prudence,
I am a single female physician in my mid-30s. I had a deep intellectual and (brief) romantic connection with my much older mentor. Now, I can’t figure out how to let go. "John" is over 20 years older than I am, divorced with grown children. He’s taught me everything I know about being a doctor. We delighted in each other’s friendship and a mentor/protégée relationship for most of the past decade. I was moving away after my fellowship and we both became emotional that we couldn’t see each other regularly. We got romantically involved at that point and it felt so natural. We acknowledged our love but John said no to a committed relationship. I want marriage and children and he said he wanted neither again. He said he wanted me to be with someone who could give me all that. He’s also a self-declared womanizer. Since then we continue to have confusing contact. He provides me with guidance in practicing medicine. We have intimate chats, and occasionally physical intimacy when he comes to my city. I know it’s best for me to cut him out completely, but it’s so hard to let go. I can't imagine how I will practice medicine without being able to call him, and I would miss him as a friend. How do I keep the connection but ready myself to pursue a real romantic relationship?

—Heal Thyself

Dear Heal,
This is revealing examination, doctor, of the dark side of mentorship. No, it’s not just the matter of you two becoming lovers. It’s that your dependence on John is keeping you stuck psychologically. You can’t imagine making your way in your career without the constant advice and reassurance of someone you have elevated to godlike status. John may indeed be the William Harvey of his day, but surely he must hope that as he ages and medicine advances, you will eventually surpass him as a clinician. You already know consulting with colleagues makes you better at what you do, so at this point you should have a circle of people you turn to, not just one oracle.  For the sake of argument (sorry to inject this thought) let’s say John suddenly drops dead. You’d feel bereft, but you wouldn’t close up your practice because you can no longer turn to him for advice. If for your own emotional health you need to cut him out of your life, recognize you will go on just fine. Being clear about that may give you the strength to maintain a just-friends relationship with John. Stop having sexually charged conversations, and sex, with him. Tell him he’ll always have a special place in your heart, but you two have to go back to being colleagues. Since he’s admittedly always juggling a bunch of women, it perhaps will come as a relief to him. I’m no doctor, but the medical facts are that since you are in your mid-30s and want children, you don’t have a lot of time to waste in finding a partner. Don’t “ready” yourself for a life post-John, start living it now.


Dear Prudence,
I have belonged to a local play group for moms and tots for the past three years. Recently a man joined, and he is the only stay-at-home dad who has ever become part of the group. A fellow group member recently told me that she found out that he is not who he appears to be. He said that he is a physician assistant, but he is only an EMT. He also lied about his wife's profession. After a little more digging we discovered that he is a convicted felon (he spent two years in prison) with charges dating from the 1980s to 2005. I don't want to stir the pot, but I am concerned about his attending play dates in friends' houses. Do I out him or let this ride? Help!

—Desperate Housewife

Dear Desperate,
Only recently I denounced the "ugly and pernicious" assumption that all men are criminals unless proven otherwise, so thanks a lot. This dad has a long rap sheet, but I wish you’d been more specific about the offenses. You don’t sound too alarmed, so I’m assuming you didn’t find he was a violent offender. The charges do run over quite a period, but they are from a long time ago, so maybe this guy had a rough start in life and engaged in petty crime with a bad group. But now he’s married, trained for a career, is a father, and has made a fresh start. It could be his lies about the work he and his wife do are actually more just exaggerations so that people in your group will think he and his family fit in. Sure, it’s also possible he’s a dishonest and bad guy, but he’s eight years out with no involvement with the law. I think that entitles him to the benefit of the doubt on gossiping about his past. However, you have a legitimate concern about inviting a relative stranger with a record into people’s homes. Since it’s summer, I think you should suggest your group meet at outside venues so the kids can run around. That way, you can all get to know this father better. If it turns out he makes people uncomfortable, when the weather turns you can always quietly reconstitute your group for mothers only.


Dear Prudence,

—Lactating Lady

Dear Lactating,


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