How to Do It

The Man I’m Seeing Says He Feels “Guilty” for Sleeping With Someone As Young As Me

I just don’t understand.

Woman pursing her lips with a question mark next to her.
Photo illustration/animation by Slate. Photos by Getty Images Plus.

This column is part of Advice Week, Slate’s celebration of all things advice.

Sometimes, all you need is a different perspective. So this week, our columnists have swapped fields of expertise. In this edition, Jamilah Lemieux, a Care and Feeding columnist, handles your sex questions.

Dear How to Do It,

I am a somewhat young woman and met a man who is considerably older than me a few months ago. This particular fling was very clearly defined and outlined, in my opinion, because of the age gap and associated complications that would come up with that.

In the beginning, he was very on board with all of this, but almost immediately, he began going back and forth on whether or not he actually wanted to do this and the guilt he felt from having sex with someone as young as I am. The first time he brought this up, I was perfectly willing to call it off, but he said he still wanted to, so we just continued on. I just can’t understand why he keeps bringing up whatever guilt he feels all of the time. If he feels so guilty, why doesn’t he just stop? I can’t tell if this is some form of attempted emotional manipulation that I am falling prey to or if he just genuinely changes his mind this often. How do I tell the difference?

—Young and Dumb

Dear Young,

I can’t tell you if this man genuinely feels guilty about your relationship or if he’s just using that line of talk to manipulate you, but I can give you a few questions to think about that may help you decide how to move forward. For starters, do you think he should feel guilty? Do you think this relationship is inappropriate? Is the relationship taboo simply because most people wouldn’t do it, or do you think it could legitimately be less than OK? Do you feel that you have agency in this dynamic? Is he in a position of power over you? Does he treat you with respect and make you feel safe? Really consider the age gap between you two—I can’t weigh in on it without the details. But if any part of you agrees with him that the paring is wrong, then you need to get out of there.

It’s possible that this guy is simply having a hard time coming to terms with the age difference—just not a hard enough time for him to let you go. If you feel completely comfortable with what’s going on between the two of you, then let him know. Share with him that you feel safe, empowered, and capable within the relationship and that you’re also clear on its limitations. Also, understand that his lack of clarity about how he feels may mean that he could abruptly walk away from the situation at some point. If you enjoy his company enough to put up with his handwringing, then by all means keep going.

But if his shame routine turns you off, then there’s no need to put up with it longer. It doesn’t sound like this affair was meant to go the distance; accept that your best days with this guy may already be behind you and consider setting your sights on someone who can confidently take you as their lover with no apology.


More Advice From Slate

I have been looking for someone who both shares my sexual interests and is a good human being overall for the possibility of a long(er)-term relationship. While I feel like I might have found this person recently, the fact that they are a high school teacher and have a strong interest in role-playing student-teacher and my own dating history make me wonder if this kink is a healthy outlet for someone in their position or a foreshadowing or indicator of something more sinister.