Brandy Jensen, The Outline’s Power editor, has made a lot of mistakes in her life. Has she learned from them and become a wiser person as a result? Hahaha oh gosh no. But it does leave her uniquely qualified to tell you what not to do — because she’s probably done it.

Dear Fuck-Up,

My brother, who is turning 30 this year, has started to date an 18-year-old. I wholeheartedly disapprove of this relationship. It's not that I think it's inappropriate for him to be dating someone younger than him, but I find it predatory that he would entertain being in a relationship with someone who is basically still a child (I mean, he hangs out in her freshman dorm room). He's very defensive about her age the few times I've brought it up with him, and now shuts down any conversations about it.

Some additional backstory — my brother was recently in an abusive relationship that lasted a little over four years, which ended with me flying to him and calling a mobile crisis unit to get him out of it. Since the end of that relationship, he's gotten back to his normal self — going out with friends, traveling, spending more time with our family.

I want to give him some leeway since I know he recently got out of that terrible situation but I just can't find any silver lining in him dating someone this young. Similar to his previous relationship, no one in my family approves, but also no one knows how to confront him about it. I don't want to push him away now that our relationship is in a much better spot. Is it wrong for me to keep bringing it up with him? Am I supposed to let him figure it out on his own?

Sincerely,
Concerned

Dear Concerned,

I think anyone who is even passingly familiar with me and my whole deal would be able to confidently guess that I dated a lot of older men when I was in my late teens and early 20s. Of course, at the time I thought it was a sign of my stunning wit and advanced intellect that men with prostate concerns wanted to be in a relationship with me. And while I still maintain my wit was stunning and my intellect advanced, I must concede it had much more to do with my perky tits.

Were all of these men predators? No. My college professor certainly was, but in addition to the age gap he was leveraging a built-in power dynamic to his advantage. And of course there are many young women out there perfectly capable of making their own sexual decisions who are ill-served by the infantilizing desire to protect their virtue. But, as you correctly point out, your brother’s new girlfriend is quite literally barely legal. I’m completely comfortable making a blanket rule against 30-year-olds dating teenagers, no exceptions.

I think you should continue to talk to him about this, but I would avoid broaching the topic from the position of firm, ethical disapproval. Few people react well to being told they are creeps — least of all creeps themselves. Instead, I would start by asking him what he sees in this girl, er, woman. It is very understandable, given his last relationship, if he was left feeling vulnerable and fragile. So perhaps a relationship he can view as a bit of harmless fun seems safe to him, for now.

What is not acceptable is taking comfort in someone who is pliable, someone who is not yet a fully formed person able to articulate her needs or desires. If you can get him to open up about what, precisely, he is getting from this arrangement, you might be able to lead him to the conclusion that whatever benefits there are for him will likely come at some sort of cost to her. You don’t specify how recently his abusive relationship ended, but I think it’s quite reasonable to let him know you have some concerns about how it may still be affecting his judgment.

Failing that, you can probably still rely on one bedrock truth: while the concept of older men dating much-younger women is only sometimes unethical, it is always deeply fucking corny. I can guarantee you some of her friends have very funny nicknames for your brother. One or two times being asked if she’s seen Manhattan and she will invariably realize that rather than continue to date him, she can just get a fake ID and buy her own booze.

Love,
A Fuck-Up

Have a question for A Fuck-up? Email DearFuckup@theoutline.com