‘She’s In Double Digits While I’m Still Batting In The Eight Hole’

Virtual event alert: Tomorrow I’m moderating a book talk about about how to be in your 20s and how those years affect the rest of your life, personally and professionally. The book is called “The Rocket Years,” and I found it quite helpful and super interesting (despite being in my 40s). You can sign up to come and ask questions of author Elizabeth Segran. We’ll probably talk about how COVID has changed life for people in their 20s who were (before all of this) dating a lot of people and trying to find a partner. Also, of course, you can send your own relationship questions to [email protected].



I met a woman through mutual friends a few years ago and felt an instant connection. She was at the tail end of a relationship, and she mentioned that she was interested in me. I didn’t see her for a while, nor did I pursue it right away because I didn’t want to be the rebound. I made an innocent comment that I was waiting for her to get “clean.” It was a joke, but girls talk, and next thing you know she ended up dating another gentleman. I was a little upset, but we ended up linking up after that. I initially gave her a hard time for squeezing another guy in before me.

Long story short, we’ve been dating for two years and things are starting to get serious. Our friends are all getting married, and I think it’s putting the pressure on us. I told her I’m not ready yet. I’ve noticed she’s been more flirtatious around other guys in front of me now. Are you noticing a trend? I mean, she is one of those girls that is full of life and everyone loves her, but I question her loyalty if we take the next step. We had the how many “number” talk and she’s in double digits while I’m still batting in the eight hole. Doesn’t get me overly thrilled to meet her at the altar. Do I need to get over this, because what’s the alternative? She wants to work things out, and is even paying for couples therapy, which I can’t take seriously. Where do I go from here?

– Stranded on the Vineyard


Honestly, if you’re counting this woman’s sexual partners, shaming her for seeing other people before she started dating you, and monitoring her behavior when she’s around other men, please let her go.

You’re supposed to be in love with who she is – the person she could be as a forever partner. But you seem more focused on how her history affects how you feel about yourself. You claim the “clean” comment was a joke, but everything in this letter suggests you were not joking at all. If you go to therapy on your own – and I hope you do – read your letter out loud and unpack every sentence. Why do these numbers matter to you? What do they represent? How do you define loyalty? What kind of marriage do you want and can you have it with this woman?

All I can say is that therapy can be helpful. You don’t have to decide whether to take it seriously – you just sort of go (virtually, these days) and say some things that are honest. I mean, you’re writing to an advice column, so clearly you have some interest in processing how you feel (unless you decide to write this off as an exercise in entertainment.) A professional can help you figure out why you’re so threatened by a woman who knows what she wants and has experienced life outside of her relationship with you. They might be able to help you get over yourself and figure out how to have more productive conversations about marriage, your perception of your girlfriend’s flirting, and how to plan a life together – if that’s what you want.

Once again, you can also let this woman go. You can forgo her company to look for someone else. That is always an option. At this point, that might be the kindest thing to do.

– Meredith

Readers? Can you help this LW with … whatever the problem is? How should this person approach couples therapy?

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