Jumping In, Not Pushing In: Helping Someone with Dating Doubts

Last post , I shared the story of Sruly, a young man struggling to get engaged, and the clinical approach to helping him. (As it happens, I called Sruly to ask his permission to share his story with de-identified information and he told me that he proudly shares his story so many years later, and would even allow using his real name, which I did not).

The question is for the layperson, how do you help the Sruly in your life? Whether a child, friend, or student, what should you be telling him or her? The natural inclination is to make the person feel better, offering hopeful advice: 

“She’s an amazing girl!”

“Don’t overthink this.”

“I know you’re nervous now but after the wedding it will be better.”

These words come from love and concern. But when the person is struggling with Relationship OCD (R-OCD), a specific form of obsessive anxiety that fixates on doubts in dating, reassurance can unintentionally do more harm than good.

The Reassurance Trap

R-OCD is a subtype of OCD that focuses on romantic relationships. The hallmark feature is obsessive doubt: repeated, intrusive questions like “Is this the right one?” or “What if I don’t like them enough?” For the person with R-OCD, these aren’t fleeting thoughts or worries. They’re mental loops that generate distress, and the more the person tries to “solve” them, the more stuck they feel (because they’re usually unsolvable).

Enter reassurance.

When a mentor or friend tries to soothe the doubt with a well-intentioned comment like “He’s a great guy, don’t worry,” it offers temporary relief. But it also teaches the brain that doubt is dangerous and needs to be eliminated. This reinforces the obsession, feeding the cycle.

Worse, if the person starts relying on reassurance from others, they may lose touch with their own instincts. I've had the unfortunate experience of sitting with a client who regretted his decision to marry his wife due to pressure he received from others, and once lamented to me, “Maybe my rabbi should have married her, but I should not have.”

So How Can I Help?

My rebbe, Rav Mordechai Finkelman, once shared a powerful story that perfectly captures how to support someone with R-OCD in the most healthy way possible, balancing a tiny dose of reassurance with higher levels of honesty and empowerment. 

A young man asked him whether he should marry the girl he was dating. Rav Finkelman responded:“If my son brought home a girl like this, I’d be dancing on the table. But only you are going to marry her, so it doesn’t matter how excited I would be.”

That represents the model people should follow. Supportive and positive, but honest and careful not to substitute the rebbe’s feelings for the student’s.

Helpful Tips

If reassurance backfires, what should you do instead? If you’re a parent, friend, or mentor, here’s what you can do. The first two tools below are within your reach; the latter two may be best left to a trained therapist.

- Validate their struggle:

“This sounds really hard. I can see you’re in a lot of distress.”

- Reflect autonomy:

“Only you can know if this feels right to you.”

- Encourage inner listening:

“When the anxiety isn’t loud, what does your gut tell you?”

- Gently question the reassurance loop:

“I’ve noticed this question keeps coming back — do you think any answer would make the fear go away?”

These responses affirm the person’s feelings without feeding the compulsive need for certainty. It’s hard to sit with someone in pain and not offer answers. But doing so, being present without fixing, is often the most powerful form of support.

Offer your presence, not your conclusions. Affirm the person’s strength rather than solving their doubt. You can say: “I don’t have the answer, but I believe you can find your way through this.”

In a world of high-stakes dating and permanent commitments, it’s natural to want clarity. But when doubts become obsessive, the path to peace is not through more information — it’s through learning to live with uncertainty. The most loving thing we can do is help someone reconnect with their own voice, not speak over it.