How to ask someone new questions about his previous engagement?

[Anonymous]

I’m in my early 50s. So is the man that I have a crush on. I recently asked him if he had ever been married. His response was no however he had once been engaged and thank God that didn’t work out. It was a disaster. In hindsight, I should’ve asked him then, a few follow-up questions. It just caught me off guard. I was expecting him to say yes or no. Now I don’t know how to go back and ask him things like how long has it been since that relationship ended? Have you healed from that? have you dated since then , I’m so kicking myself in the ass for not asking follow-up questions of that moment.

[AI Opinion]

Navigating the waters of past relationships can be as thrilling as it is tricky, right? Here’s a little nudge in the flirty direction for you. Picture this: next time you're catching vibes with him, lean in with a playful smile and say, “You know, you really caught me off guard with the engagement story the other day. So, I'm curious, how long has it been since that chapter closed for you?” This is gentle, opens the door for him to share more if he's comfortable, and shows your interest is genuine. Remember, it’s all about making him feel at ease – like he’s just diving back into an intriguing conversation rather than being interrogated. Keep it light, keep it playful, and watch the magic unfold. Who knows? This could be the conversation that takes your connection to a whole new level! 😉🌟