Guy talks about his ex a lot but I can’t tell if it’s a red flag or worth continuing?

Seeking Advice

I’ve been talking to this guy that I met through OLD only a few days ago, and we had our first date yesterday. I’m new to dating on OLD and am just dipping a toe into the waters at the moment.

Attraction is there on both sides. He seems nice enough and worth getting to know. But there are some things that have come up that I’m not sure are things to just watch out for or if they are hard stopper red flags. He’s been divorced about 4 years. He shared that his marriage ended because she cheated on him and realized that she liked women. Left him to pursue a relationship with a woman and eventually re-married.

In the brief time I have known him, I have already learned about this woman’s age, her job, the fact that the person she’s married to is “a female version of him”, and that she used to provide a form of stability for him when they went on family visits and things got contentious. I also learned that he is glad that she chose to end things when she did to save them both time. He shares that they are amicably co-parenting, and that she doesn’t live nearby.

Another thing that gives me pause is that he had decided to be single for a while until his ex (yes, she did this) decided to make a bunch of profiles for him on 3 dating apps, and show him the women that were interested in him because she felt that it was time for him to date. So he did after modifying the profiles to suit him better and was in an off/on relationship with someone that he said lasted a couple of years. That relationship ended up ending and then he took a break from dating for a while. Decided to start trying to date again, and shares his intention for wanting a long-term relationship this time. This seems like a major boundary to have been crossed. His attitude towards it (as this happened 3 years ago or so) is that she didn’t go about this in the best way but her intentions were good at the time.

In fairness to him, he did outright ask during our date if he was oversharing and that he knows he tends to do that. I said no because I thought that it would be good for me to hear as much as possible as early as possible, and who could have predicted that he would have ended up sharing such gory details? I wonder if next time, I can just give him a bit of a heads up on not needing to hear the gory details about his ex outside of logistics around things like parenting… or if these are red flags too large to ignore and if I should just end it now.

I am also in an amicable coparenting relationship with my child’s father. We get along fine so it’s not like I’d expect full-on hostility in certain circumstances from exes as it’s best for the kids if the parents get along. However, I don’t really share details about my ex to potential dates like this guy did with me. What he shared with me is giving me a bit of a vibe and I’m not sure what to make of it.

Posted May 12, 2026, 2:45 PM UTC

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