Past relationship regrets

Bare with me this may be a bit long.

My parents have been married for over 40 years but that doesn’t stop my dad from constantly talking of this woman that he dated before my mom. Apparently my dad didn’t treat this woman right; (we’ll call her Debbie). To this day he will say how he wishes he had done different with her and not been so awful with her, he has even looked up where she lives now. Never mind that it is completely disrespectful to my mom to constantly speak about this woman 40+ years later.

Well recently my brother and his gf broke up and he has been really upset about it. We had all told him he should’ve married this girl a long time ago but he said he wouldn’t be forced into a marriage based on others thoughts and opinions.

This past weekend he was talking to my husband and came to the realization that he may be repeating our dads past mistakes with a woman and that he will live to regret it saying perhaps his gf was his “Debbie”. My hubs responded to his comment by saying we all have our own Debbie. I thought this was interesting because I cannot say that there is anyone in my past that I have regrets to this day about how the relationship went or ended. I asked my husband so who was your Debbie? In which he changed the subject and tried to tell me who my “Debbie” was. I told him he was wrong because I don’t have any regrets on how things went or ended because I made peace with it and that person. I then asked him again who his Debbie was and he says you really want to know? And then he proceeds to tell me about a girl he dated in college who he had never mentioned before as an ex. Apparently she tried to get back together with him when we first started dating and even offered to move to the state to be with him because she could work wherever since she was studying to become a dr, he then adds that she’s probably a dr now. This is the first time I had ever heard of her or been told anything about this relationship. So out of curiosity I looked up this girls name to see if he was still friends with her. It was a mutual agreement to remove exs and past ppl we had had relationships with off of our fbs when we started dating/married because what is the point of keeping track of someone you had intimate ties with? Plus it caused issues with us when we were dating over him still talking to these women and constantly questioning any man who liked my pictures or posts. Well low and behold he is still friends with her and while she studied microbiology she did not become a dr because she owns a boutique now.

So what was the point of him saying to me that she is probably a dr now when he would clearly know that she most definitely is not? It’s bugging me that he is still friends with her even though there is nothing going on it’s just the fact that he admitted to having regrets with her. Why would he even bring this up or make these comments besides to hurt me and almost rub it in my face? And how do I bring up the fact that he is still friends with her on fb and likes her posts?