To date a guy with 2 kids to two different women?

[elephantsbreafh]

Or am I being horribly judgmental?

I’m a single parent myself. He’s early 30s, 6 and 3 year old kids. Has them every weekend. We’ve chatted a lot and he’s gone into almost too much detail about the past relationships, maybe he’s just really honest (a good thing) or maybe he’s trying to paint a different picture, as the story was really quite elaborate considering we haven’t met. Lots of detail about how they were engaged, she went behind his back and started booking everything for the wedding, then he found a huge bag of pregnancy tests and she’d stopped the pill and gotten pregnant. They split up, then his next ex got pregnant at the end of the relationship. I just feel a little off about it at all. He’s adamant he doesn’t want any more kids, which is fine by me.

I’ve been single for a very long time, and had some awful experiences online dating so trying to get some outsider opinions on whether this is a red flag, or am I being overly cynical/cautious.

This. The guy I dated did the same.

I mean it could just be that he knows he's going to be judged for having two (young?) kids by two different women and he might be oversharing to try and explain it away (think Ross from friends and his "three divorces" excuse for not annuling the wedding with Rachel, IYKYK). But if you already are questioning him and his sincerity why get more invested? Also I wouldn't date someone with kids (regardless of number of baby mummas).

I would steer well clear, his situation sounds very messy. And the whole ‘wedding behind his back’ story is ridiculous!

Trust your instincts! You don't need this. It might be different if you met him when you were both older (and him wiser), but right now it would be best if you tried to meet someone with no children. It shouldn't be too difficult as from what you've said, you haven't known him in person for long.