Ask Mom & Spawn!

Ask Mom & Spawn: I Kissed Someone Else Before my Husband Proposed…and I Still Feel Guilty Years Later

Anonymous wrote in because she was angry that her boyfriend didn’t propose to her and kissed someone else, but now she’s married and wracked with guilt! What should she do?

My now-husband and I dated for 5 years before he proposed. By year 5, I was frustrated with waiting for a proposal, but wasn’t ready to leave because I love him so much. During that year, a guy asked me on a date, and I went, and we kissed. I never saw him again, but I am still so racked with guilt over what happened. We’re now several years into a happy and wonderful marriage, but I still haven’t forgiven myself for what I did. Should I tell him? I don’t want to hurt him, and a part of me feels like I missed the boat for coming clean on this a few years ago. – Anonymous 

@CrazyJewishMom: You let that boat keep sailing in the other direction, and never look back! Take it to your grave.

@KateFriedmanSiegel: Well, it’s a globe, so at some point that boat is going to sail back around to you and bite you in the seasick ass (to keep this seafaring metaphor going!). I don’t know, this is a tough one.

@CrazyJewishMom: Well, I do. The only thing you’re going to accomplish if you tell him, is pain You’re committed, you’re not throwing your lady bits at every sperminator who crosses your path, you made a one time mistake that has no relevance to the beautiful future you can have together. Don’t hurt him to make yourself feel better. And frankly, he made you wait five years for a commitment? He’s lucky you didn’t castrate him with a rusty butter knife.

@KateFriedmanSiegel: MOTHER!

@CrazyJewishMom: Oh come on! The last part was a joke.

@KateFriedmanSiegel: I really believe that honesty is the most important thing you can have in a relationship, and so I definitely understand where you’re coming from with the feelings of guilt. I do see my mom’s point (not re the rusty butter knife, but the one about not causing pain to make yourself feel better), but I think it’s ultimately a very personal decision. If you tell him, it will be very painful and it will take time to regain trust, but you may come out the other side stronger. That said, you know him best and understand how he will respond. If you think he would take it horribly and are committed to an exclusive future together, I do see why you might not want to tell him.

@CrazyJewishMom: Don’t do it. Don’t risk the entire relationship over something you know was a one time mistake and is ancient history. Besides, you didn’t even sleep with the guy! Move on. Be Happy.


Want more advice from @CrazyJewishMom & Spawn? Listen to our podcast here, and tune in every week Sunday at 5 PM ET on the @AskMomAndSpawn Instagram page for our live advice/ podcast recording sessions! We might just answer your question live!

You can also submit your questions below for the advice column! AND follow us:

@AskMomAndSpawn on Instagram, Twitter, and Facebook!

Your Name (required)

Your Email (required)


Your Message


By making this submission, I hereby acknowledge that I have read, understand, and agree to all the terms and conditions set forth herein.

For qualified advice, please visit this website for resources.

If you are a victim of domestic violence, please visit this website for resources or call 1-800-799-7233.


The Latest

To Top