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When is a good time to tell the guy you have been talking to and really really like, about your past? I was engaged before and it did not work out. And how do I bring this up without being a downer

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after sex

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Wear extremely sexy lingerie and tell it right before sex. He'll feel lucky that your engagement didn't work out.

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But isn't the past passed? What do you want to achieve by revealing your past? Commitment or not, it's all up to your partner's interpretation. If you were married before, that's a whole different story. Engagement...errr I say keep it to yourself. Sounds like opening a can of worm if you bring it up first

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the fact that you explain him as "the guy you have been talking to" instead of a boyfriend or SO leads me to think this is not the right time to bring up past relationships. unless you've already talked about past serious relationships. could be an interesting way to segueway into what you're looking for in a long term relationship. but unnecessary if you're not serious yet

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When I was dating my now-wife I found out she had been married before because her old last name was on a credit card that I noticed her put down. Didn't matter to me, but any way you bring it up will be less awkward than that.

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Casually slip "my ex-fiancée..." into a random conversation

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Can't speak for all men but for me I don't like asking about someone else's past, so if your guy is like me then the best way to bring it up might be just start a more serious conversation about what you expect in relationships and depends on how things go in that conversation you can bring up that topic?

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"segueway"

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The ue is silent

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You should tell him exactly what you wrote here: that you aren't sure if it's the right time but that you'd like to share some things about your past with him because you feel it's important. If he makes this into a negative thing, or takes it the wrong way, it's a red flag and very telling in itself. Why would you want to be with someone who didn't understand the conversation, got defensive/insecure, or took it the wrong way? It's not a big deal, and he shouldn't make it one. Don't overthink it - bring it up when the time feels right. 🙂

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Your past is your past. Focus on the present and future. People are interested in your past to pass judgment. At some point feel free to share, till you are comfortable the past can stay there. Much more interesting to create new memories

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Find out about his past before revealing yours.

^That's already a downer 😆

I already know about his past. Never married or engaged before.

Why do feel you have to bring it up?

I feel like wouldn't I want to know if someone I am seriously talking to was in such a commitment before? I may be overthinking.

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