Dear Lizzy, I Was Previously Engaged... At What Point Should I Mention That To A New Girl?


Dear Lizzy,

I’m 29 and got engaged to my college girlfriend when I was 26. We broke up a few months ago (after being on and off for over a year) and I’m now dating again. Our breakup was mutual as it just wasn’t working out and we both felt it was time to separate. I’m excited to start dating again and move on with my life, but feel like no one is looking for a guy that was engaged before.

How do I bring up to a date that I was engaged? I don’t want to mention it on the first date and scare them off, but also don’t want to make them feel like I’ve been hiding anything when it eventually comes up.

Should I not mention anything on the first date and if it goes well then tell them on the second? If you like a guy and he was engaged before would you instantly not like him anymore?


No Longer Engaged

Dear No Longer Engaged,

Not one mature woman will care that you were previously engaged. If anything, it shows that you can commit and women looking for that sort of commitment will see it as a good sign. The fact you also knew when to call it quits instead of getting married just because you were engaged, is also a positive sign.

The only questions a woman should have is… why did you get engaged to begin with? And why were you engaged for 3 years?

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These are reasonable questions and I’m sure your answers will be reasonable (“We felt like it was time.” “Our families were pressuring us.” “It’s what you do in the south.” etc, etc.). More importantly, it sounds like your breakup was very mature and responsible, so make sure you emphasize this part when you’re telling her what happened.

I personally don’t think this information is necessarily the best first date material, but if you guys start talking about past relationships for any reason and she asks, you have to tell her. Otherwise if you wait too long it’ll look like you were intentionally hiding it from her and that makes it a much bigger issue than it needs to be.

Lastly, don’t be embarrassed about your past. You’re almost 30 years old and everyone in their 30s has some sort of story, either a mistake, a long-term relationship gone sour, or a challenging lesson learned. You shouldn’t be afraid to share that with someone new because at the end of the day, it’ll be this past relationship that will make you better in your next relationship.

– Lizzy




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