Dear Kiki: Married man minefield

Questions about love and sex in the city of Iowa City can be sent to (queries can also be sent anonymously using this form). Questions may be edited for clarity and length, and may appear either in print or online.

Dear Kiki

Hi Kiki,

I’m in love with a man who is much older than me and happily married. I used to work for him, so telling him how I felt then was out of the question. Now I’m working somewhere else, he’s moved away, but we still email almost every day. I’m not sure if he knows how I feel; I’ve been obvious about it, but I’ve never been direct. I don’t want to hurt him or his wife, but I feel like I’m going to go crazy if I don’t do something different. Should I tell him? Stop emailing and try to move on? — Sad Sack

Hi Sack,

I am sorry dear, truly. Because this trope rarely plays out like a Hollywood romance. More often it plays out like reality TV: trashy, absurd and ultimately made up of empty calories of emotional energy. Don’t bother spilling your sad sack of beans all over your keyboard for that mess!

You wonder if he is interested? Does he know you’re interested? Are you being obvious enough? None of those questions matter because you’re talking about an older, married man who was your boss and lives far away. Nothing about your email leads me to believe that this man is either interested or available. Think this one through, tootsie.

If, as you say, he’s happily married, and he isn’t into you like that, then telling him your feelings could seriously disrupt the friendship/mentorship you have now. You’d be risking outright rejection and rebuke. If he did want to have an affair, do you think you could follow through with that? Listen to wise old Kiki here: the “Other Woman” is a bum deal.

Even if your feelings are mutual and he is interested in having a romance with you, would you be able to depend on or trust a man who is cheating on his wife? Suppose he wanted to pack up and leave his wife for you — are you in a position in your own life to have a long-distance relationship with a much older man who is untrustworthy, going through a painful and costly divorce and probably having a midlife crisis? Didn’t think so.

Whether you like it or not, this guy is not for you, and confessing your crush will only erase a reference from your resume. It might be a good idea to ease the frustration and cut off communication for a while until the passion fades from your typing fingers.

But look: You won’t go crazy, and the world won’t end. Feelings are not facts; they are all yours to manage and deal with, and they are known to change rather quickly. So let the feelings do their thing to you while your old buddy sits blissfully unaware, miles away, at home with the wife. When you’re ready, you can go searching for a love interest who is appropriate for you to date (i.e. not your boss, not your dad’s age and not married). xoxo, Kiki

This article was originally published in Little Village issue 200.

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