Dating a Mentor Who’s in a Relationship Will Only Bring Double the Trouble

Demetria Lucas D’Oyley
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Dear Demetria:

I’m a 30-year-old female, and I have a male mentor who is in his mid-50s. He has been instrumental in helping me navigate through my professional life. We have great conversations. I feel there is a connection. I’m not sure if he feels the same. We talk about both personal and professional things, we’ve hung out during happy hours and we text regularly. I know he has a girlfriend, but they do not live together and he does not always talk about her to me.


I have a huge crush on him. I am torn between not letting it cross the line but also wanting to see where else it can go. One of the biggest dilemmas is that he is very connected in the community, and I am starting to do more work in the community as well, so we are connected to some of the same networks. How should I continue this relationship? —Anonymous

Pursuing this man is a mess waiting to happen. I get a lot of questions from women, sometimes men, about pursuing people who are in relationships, even marriages. No matter what or how many details are given or how hard you try to justify it, the answer will always remain the same: No.

People in relationships, even the unmarried ones, are not available. It doesn’t matter if both parties are miserable, if they’ve cheated before, if their partner doesn’t mind or if they’re long-distance. They are still committed to someone, and if one or both wanted to be uncommitted, they would be. Something is keeping them together. And as long as they are a pair, leave both of them be.

As for your trying to date this man in a relationship? You think you want this, but you don’t, even if he is willing to cheat with you. That would mean he has a massive character flaw and is very comfortable lying to and deceiving a person he says he cares about. He would also feel the same way about lying to and deceiving you. You know that, right?


But even if he weren’t in a relationship, this would still be a poor decision. As a general rule, it’s a bad idea to get your meat where you get your bread.

You say that this man has been “instrumental” in your career and has the connections to benefit you further. But what if you date him and things go south, personally? You do realize that the access to his connections would be over when the relationship is, too, right? Are you OK with that likely possibility? I say “likely” because most relationships don’t make it to marriage, and you would be gambling with a man who is willing to cheat on his girlfriend with you.


What if he bad-mouths you to this circle of friends, where he has so much clout and you are a newbie? Are you OK with losing access to that group, not because you don’t have the qualifications to enter but because of whom you dated?

Overall, this isn’t a good idea if you hope to keep access to his mentorship. However, if you are fine with figuring things out on your own and putting your connections in jeopardy, at least wait until his current relationship is over before pursuing him. In the meantime, keep your interactions cordial, of course, but draw a line in the sand to denote the boundary that must not be crossed.


Demetria Lucas D’Oyley is a contributing editor at The Root, a life coach and the author of Don’t Waste Your Pretty: The Go-to Guide for Making Smarter Decisions in Life & Love as well as A Belle in Brooklyn: The Go-to Girl for Advice on Living Your Best Single Life. She answers your dating and relationship questions on The Root each week. Feel free to ask anything at

Previously in Ask Demetria: “Should I Be Angry That I Might Be My Husband’s 2nd Choice?

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