Is he a red flag?? 🚩

My first love man we never dated but I really liked him and I heavily fw him he was my friend for about two years but I noticed when he dates a girl it doesn’t last very long and every time a girl goes out with him, she unadds him on everything and will either get married to someone else, get pregnant by someone else or just do what I’m doing stay single. Is this a red flag?? I feel like the women he picks are not nice to him, he always picks the bully type girls and I don’t get why because he’s not that way at all but it makes me wonder is he doing something idk about?? He also doesn’t want to use his certificate he got from trade school because he hates it which is fine but why are you telling me you want four kids but you don’t want to make more income?? He chooses to work customer service when he really doesn’t have to and he could easily make decent income with his certificate. I mean he might be using it now because we haven’t talked in years but sometimes I wonder because man he’s beautiful like he’s not ugly at all. He also was a great friend and really sweet to me. He doesn’t pick the best people to date (he could’ve picked me but for some reason he never asked me )