Common ways daters self-sabotage—and strategies to get past the hurdles

Sherry Zimmerman, J.D., M.Sc. and Rosie Einhorn, L.C.S.W.

When faced with another failed shidduch, some daters simply dismiss it as “not bashert” and move on. And that may be the case. Sometimes, though, they’re the one preventing shidduchim from moving forward. Two seasoned dating mentors, who are also psychotherapists, share the self-sabotaging behaviors they see most often — and strategies for getting past them

"I don’t know what to do,” Shevy* told us with a sigh. “I’m ready to go on a fourth date with Eli, but out of the blue I got a ‘yes’ from Shmuel. I’ve been dying to go out with him for two years. He’s everything I want, and if I don’t meet him now, he’ll date the next girl. What if it doesn’t work out with Eli? I can’t lose this chance.”

During the decades we’ve been mentoring daters, we’ve seen this scenario unfold countless times. “Shevy, you’re telling us that even though things have been going well with Eli, you’re ready to drop him because your fantasy life with Shmuel might come true. What’s wrong with this picture?”

“You tell me,” Shevy responded defensively. “I don’t think there’s anything wrong. Eli’s a nice guy, and there’s no reason for me to stop seeing him. But there’s also nothing to keep me there. And Shmuel’s exactly what I’m looking for. I’ve been waiting for a ‘yes’ for so long.”

We empathized with Shevy. “We can see why you want to date someone you’ve been waiting for. That said, there’s no guarantee that you and Shmuel will get to a second date. On the other hand, you see good things about Eli, and your connection is just starting to develop. If you stop seeing him now, you’ll never find out what could’ve been.”

Shevy looked pensive. “It’s funny you should say that. In the past, I’ve done exactly what I want to do now — end something at this point because there’s a guy who sounds better. And, I have to admit, when I did that, it never materialized into anything. Still, I can’t stop hoping that with Shmuel it’ll be different.”

When a budding shidduch is progressing slowly, daters can get easily distracted if a new suggestion comes up that sounds more exciting — be it with yichus, family status, looks, charm, or a bio that “checks all the boxes.” They rationalize that they should jump ship on the current shidduch to date the new person. But actually, they’re engaging in one of the many forms of shidduch self-sabotage.

There are many reasons why men and women who seem to be dating for marriage repeatedly sabotage themselves to keep relationships from forming. Many of these daters usually don’t understand, or at least won’t admit to themselves, that something is blocking them from moving forward. They believe they want to be married, and they date frequently and readily, but their own actions keep them from achieving their goal.