Dear Anna,

I’m (27F) told pretty often that I’m out of most guys’ league, looks-wise. The guy I’m dating (36M) is a great person, but he’s not conventionally attractive, and he can’t stop pointing that out. I want to be clear I’m genuinely into him — I’m attracted to him, tell him constantly, and mean it. But whenever we’re out together, he often makes some version of the same joke: that strangers must be wondering what he did to land someone like me, or that the hostess probably assumed I was there with someone else and he just got lucky when she sat us together. Last week, at his coworker’s birthday dinner, he told the table that he still doesn’t know how he “talked me into this.”

I can’t quite explain why it bothers me so much, but it does. It’s not that the jokes are mean — it’s that he seems almost fixated on how we look to other people, even though I’m sitting right next to him telling him how much I want to be with him. When I’ve gently brought it up before, he insists he’s not insecure, he’s just being funny. How do I get him to stop doing this? — Not Laughing

Dear NL,

You get him to stop by saying, “I don’t like when you make jokes about my/our appearances. Please stop.”

Seriously. You don’t need to probe his psyche before you’re allowed to ask for a change in his behavior. You don’t even need a particularly compelling explanation for why it bothers you. It bothers you. That’s enough information to bring to him.

Something like: “I know you think these jokes are funny, but they make me uncomfortable. I genuinely find you attractive, and when you keep joking about how I’m supposedly too good-looking for you, it starts to feel like you’re arguing with me about my own attraction to you. Please stop.”

You don’t have to agree about why he’s doing it. Maybe he’s insecure. Maybe self-deprecating humor is his favorite way of coping with uncomfortable things. Maybe he thinks he’s being charming. Fine. His reason is his own business. But the impact is yours.

And self-deprecating humor can be a useful little psychological trick. Making the joke about yourself first can create a sense of control, a la: If I say it before anyone else can, they can’t use it against me. Lots of us do some version of this when we’re feeling vulnerable.

But self-deprecation can be a double-edged sword, especially when it negatively impacts those who care about us.

I’ve had plenty of partners put themselves down about their looks, and I’ve put myself down too. We all have down days. But it can be pretty agonizing to listen to someone you care about insult themselves regularly. Like, “Stop being mean to my girlfriend!”

And I think that’s part of what’s happening here. Let’s dig a little deeper into why this particular joke might sting.

For one thing, it asks you to keep proving that your attraction is real. You’ve already told him you’re into him. You tell him constantly, and you mean it. But every time he makes the joke again, you’re effectively being asked to provide the same evidence all over again. Eventually, “But I really do think you’re hot!” starts to feel less like validation and more like a job you’re not even getting paid for.

It also turns your relationship into a performance for strangers. Who cares what the hostess thinks? Who cares what his coworkers think? You’re the person dating him. Your opinion of his attractiveness is the one that matters.

And there’s something subtly insulting about the repeated “How did I land someone like you?” line, too. You aren’t a prize he won from a claw machine. You’re a person with agency and taste and are more than capable of determining what you want in a partner. To suggest otherwise is to take away that agency and make you doubt yourself.

When he repeatedly suggests that your attraction to him is surprising or inexplicable, he isn’t necessarily meaning to, but he’s making your choice seem less credible. You’re telling him, “I choose you,” and he’s responding, “OK, but why?”

That’s a weird position to put someone in.

It can also make you feel like you’re being turned into a status symbol. If the joke is always about how other people must perceive the two of you, then suddenly your attractiveness isn’t just something he enjoys about you. It’s evidence of his own social standing — or lack thereof. You become proof that he somehow “beat” the odds of acceptable kinds of romantic partnerships.

I suspect that’s why “I’m not insecure, I’m just being funny” isn’t particularly satisfying as an answer. Because whether he’s insecure isn’t actually the issue. It’s that he’s repeatedly making your relationship into a public referendum on whether he’s worthy of you. Which can feel objectifying, and like you’re responsible for managing his feelings about his or your appearance.

So tell him clearly. Don’t cushion it in five paragraphs of reassurance about how handsome he is. Don’t spend 20 minutes convincing him that you really, truly, pinky-promise find him attractive.

The conversation is: I like you. I chose you. I am attracted to you. And I don’t like being repeatedly asked to defend that choice.

If he keeps doing it, tells you you’re too sensitive, or turns your request into another opportunity to make himself the butt of the joke, then you have a different problem. Not necessarily an insecurity problem, but a listening problem.

Particularly about why he’s not taking your discomfort seriously when you name it directly.

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