How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous!

Dear How to Do It, 

My boyfriend “Kevin” and I have been together for a year and a half, and he’s everything I could want in a life partner. His sister spilled the beans to me that he’s been looking at engagement rings, so I expect him to propose soon. However, there’s one thing that gives me reservations.

When Kevin was in college, he … got around quite a bit. He had more than 300 encounters. The fact that he was with all these other women before he and I met doesn’t bother me. It’s the (what I think could be very real) possibility that we will get married only to have some woman show up demanding child support, or down the line, having to deal with a previously unknown son or daughter tracking him down. Given Kevin’s history, are my concerns valid, and should they give me pause when it comes to accepting a proposal from him?

—Uncertain About the Future

Dear Uncertain About the Future,

Hypothetically, surprise children are always a risk with any man who hasn’t been celibate until marriage. The fact that Kevin engaged in hundreds of sexual encounters during college absolutely does heighten your awareness of that possibility. One really useful, yet missing, crucial piece of information would be whether he consistently used condoms (and other forms of birth control) during these encounters. Sure, they aren’t 100 percent effective, but they do drastically reduce pregnancy. It’s also worth taking into account whether he checked in with partners after any encounter where the condom may have broken or slipped. Basically, if he was having sex with half of his female classmates with no birth control in place, that’s one thing. But if he was taking precautions, it’s less likely that he has a child somewhere that he doesn’t know about.

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That said, a decision to marry someone should take into account your feelings—all of them, including your worries. This concern is already giving you pause, and it’s worth doing some introspection around where that’s coming from. What’s behind your aversion to this possibility? Is whatever you find off-putting or worrisome about it also showing up in more subtle ways in your relationship? For instance, do you get the sense that Kevin was irresponsible during his college years, which is maybe reduced but still apparent now? Or do you have pretty rigid ideas about what structures families should have, and, if so, are you prepared for other unforeseen outcomes such as divorce, or untimely death? Are you strongly against having children in your life at all? And, in the event someone comes looking for Kevin later, would you be open to him having a relationship with them while you stay out of it?

I think it’s also really important to consider whether you can share this concern with him and discuss how you might navigate such a situation. If your immediate reaction is, “No, I can’t open up to him about this,” that’s the reason to reject the proposal. But if, when presented with an appropriate opening, the two of you can talk through your worries, you might find yourself more comfortable with proceeding.

—Jessica

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