Ask Erin: Should I Be Worried About Hooking Up With A Younger Guy?

"Get clear with yourself about what is important to you. And the fastest way to do that is to spend some time with yourself, not distracted by the romantic partner in front of you."

She’s made all the mistakes, so you don’t have to… Ask Erin is a weekly advice column, in which Erin answers your burning questions about anything at all.


I've been in relationships pretty much since I was 18, with very few breaks. Three years ago, I left my marriage and pretty much continued the pattern of relationship-ing up as quickly as possible. 

A year ago, I realized that was a bad plan and have been single. The thing is, I'm also 39 and want kids, so it's basically the worst time to realize I need some time off of relationships. I both want one and am afraid of one because I know this will most likely be the person with whom I have kids. 

Sort of because of this, I have started sleeping with an incredibly sweet guy who is only 25. I've known him awhile, and he's understanding of my goal of having kids and going on dates with guys closer to my age. He wants marriage and kids, but not for a while. I agree he's too young to settle down. The problem is, I've never been a hookup person, and he doesn't seem to be either. 

Strangely, I am not afraid of being hurt by him really. But I am afraid I am using him to get some confidence from his torrent of compliments about me, only to take that good feeling and find someone else. I suspect he will be hurt when I eventually do break it off to be with someone else. Of course, he might meet someone too, but I'm worried about damaging him out of my own selfish needs. 

How do I navigate a loving hookup that can't really lead anywhere? We've been at it for a few weeks. We don't just hookup, we talk and hang out, so I'm nervous about this getting too intense.


Your question is interestingly phrased — “How do I navigate a loving hookup that can’t really lead anywhere?” It’s interesting because a hookup is inherently not loving. 

You are dating this person, not hooking up. Both of you know that there is an end point, but it sounds like you are falling into a relationship pattern. 

Here’s the thing — you need to get honest with yourself about your feelings for him. As much as you say that you don't want to hurt him, my gut tells me that you’re more invested in this than you’re letting on. 

You wouldn't feel this conflict if there was no attachment happening. 

What’s good is that it sounds like you have started an honest dialogue with him about what you want and vice versa. And there’s nothing wrong with being single and enjoying that freedom. 

However, perhaps you'd be better served spending a little time alone, not relationship-ing, not hooking up, to figure out what you want in a partner and potential father to your children. 

Because doing the “loving hookup” thing you're doing is essentially the same as the serial monogamy pattern you’ve been in for a long time. What you’re doing is not taking time off from relationships.

Lastly, regarding the looming question of having kids….

There is never a “good time” to have a kid. It is scary, but you will totally figure it out. If you’re worried about the biological clock, it is a valid concern, particularly if you want more than one. But, there are several ways to become a parent, and they don’t all involve your ovaries. 

Get clear with yourself about what is important to you. And the fastest way to do that is to spend some time with yourself, not distracted by the romantic partner in front of you. 

If you have a question for me about relationships, addiction, infidelity, friendship, divorce, Sunstone, reproductive issues, or anything at all, use the contact form below or email me at As always, your anonymity is golden. xoxo

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