Dear Prudence

Help! I Think My Brother Is Being a Creep.

In We’re Prudence, Prudence asks readers for their thoughts on a question that has her stumped. The answer is available only for Slate Plus members.

Woman feeding a man a kernel of popcorn on a couch.
Photo illustration by Slate. Photo by Ivanko_Brnjakovic/iStock/Getty Images Plus.

Every Thursday on Twitter @jdesmondharris, Dear Prudence asks readers for their thoughts on a question that has her stumped. She’ll post her final thoughts on the matter on Fridays. Here’s this week’s dilemma and answer:

Dear Prudence,

My brother (a 36-year-old man) is engaging in behavior that I (a 26-year-old woman) find creepy, and I’m trying to figure out what, if anything, I can do to dissuade him. This past spring, he broke up with his 28-year-old girlfriend, and over New Year’s he introduced me to his new girlfriend.

Prudence, she’s 19. She’s just starting college, and he’s clearly her first relationship. I was kind and polite to her when we met, and encouraged her to talk about her interests, which he complained to her face are “dumb” and “childish.” My brother has always been pushy and leans towards sexism, but I’d never thought of him as predatory until now.

We’re in regular contact (although we are not super close), but I can’t think of anything I could do/say to encourage him to rethink this that wouldn’t make him dig in harder. Our parents aren’t in the picture, and he would probably listen to uncles or our grandfather, but unlike the women in our family, they see nothing wrong with it. I’m realizing my family is more sexist than I knew, and I’m trying to think of small, concrete things I can do to at least help this girl from getting burned hard by my brother, as is his habit in relationships.

—My Brother Is a Creep

Dear MBIaC,

Your dilemma is extremely difficult for a couple of reasons. First, nothing about your brother’s relationship with this young woman—the age difference, the shitty way he’s treating her, or his pushiness and sexism—is illegal, but that doesn’t make it any less disturbing. Second, we all know that, in the history of humankind, no one who is in love or lust has ever ended a relationship because someone said, “Hey, this seems bad to me from the outside.” So we have a disturbing situation that is totally allowed but probably won’t change no matter how convincing an argument you make that it should.

So what can you do to protect this girl, who is in a relationship with someone who isn’t kind and who doesn’t even have the common sense to realize that he finds his partner childish because she is closer to being a child than she is to being his peer?

Readers pointed out that there is probably no point in trying to convince your brother that he’s being creepy and predatory for dating someone so young, or that he’s being cruel for complaining about his young girlfriend’s youthful interests (even though all these things are true!).

If he’s dating a 19-year-old and complains her interests are “childish,” it seems he’s seeking a relationship with someone he can dominate and feel superior to. —@redpentweeting

There’s no reason to take this up with bro because he knows what he’s doing and he’s getting exactly what he wants: dating a naive teenager while he’s pushing forty. You can’t make him not like it. You CAN be a friend to the young lady and help her indirectly. —@wisewyzard

Indeed, you can try to influence his girlfriend. Again, this isn’t about telling her to break up with your brother or explaining how predatory this relationship is. The suggestions readers gave involved much gentler and subtler tactics—think empowering more than lecturing.

There’s a Girlfriends arc like this when William starts dating a proto Kardashian. I think the women find it’s far more effective to intervene with the gf, who eventually sees William as old and uncool and breaks up with him, if I remember correctly —@sorayamcdonald

There’s nothing she can say to the brother - but she should try as best as possible to be an ally to the GF. Stick by her at family functions, stand up for her when the brother is demeaning, let her know that the behavior is not ok. —@katedailey

Skip the brother entirely and focus on the GF. Be kind to her and establish yourself as someone she can talk to/rely on. That way, when the moment comes, you can hopefully help her realize she needs to get out. —@j_wigdahl

I was gonna suggest a modified version of this: meet up for coffee, take an interest in her as a person, & in a light, teasing way say something like “I have no idea what you see in him cuz I personally think he’s kind-of a blowhard. You’re definitely too cool for him!” —@gishmi1ish

I especially liked the ideas that involved treating her as a friend and lightheartedly planting the seed that your brother is kind of weird and uncool and not good enough for her. Even if that doesn’t work, simply being a friend, defender, and someone she can talk to will go a long way. The more you affirm her and make her feel supported, the more likely she is to eventually realize she could do better. You can’t eliminate the older person in her life who’s mistreating her, but you can be one who has the opposite effect.

Classic Prudie

I have been attracted to significantly older men for as long as I can remember. When other girls were talking about boy-band boys, I was fantasizing about Harrison Ford and Sean Connery, even in the fifth grade. Since then, nearly every male in a leadership role (coaches, teachers, bosses) has been a source of fantasies. I’m not proud to say that I acted out a few of the fantasies in real life. My father was a good dad, and emotionally supportive, so I don’t have “daddy issues.” I am happily married and hoped that marriage would end this.

But I find myself once again fantasizing about my current mentor. We have worked together for two years, and he has never done anything untoward. I want to be able to interact with men as colleagues, and not constantly have a racy dialogue playing in my head during every meeting and coffee break. I have tried to tell my husband about my “problem,” but he responds with jokes and seems uninterested. Luckily for me, I have not encountered any four-star generals, but what if I did?