Why do some men have the tendency to do this, always caught my eye?

I can only guess from my experience, which is that some men love the attention and yes, keeping their partners working harder than they do themselves, for the relationship.

One person I dated, did this with every single girl he dated his entire life, including me and after me. The one before was always the ‘love of his life’ and no one could compare. Yet at the time he was an arrogant, narcissist who was the least into the relationship.

I truly feel bad for his wife, because I’m not sure if she takes him seriously or realizes he is a serial ‘victim’ of his own bad self-interest, never happy and never satisfied with what he has. An artist who simply loves women and shouldn’t be married at all.

Honestly, I can’t say if they’re worth it or not. To me it wasn’t, I almost married him before realizing how selfish and manipulative he was. We are still friends but I keep it real with him about himself haha!
(I have to admit, I am attracted to aholes and always have been, the more confident and cocky they are with a twinkle in their eye, ladies men types, the harder I fall. I married one, too with mixed results. So did my sisters.)

The only time I think of ex girlfriends is to thank my lucky stars I got out alive :D

It isn’t just men. A lot of women do this too.

#1 rule of dating is don’t bring up an ex.

I had a coffee with a woman a few months ago, and all she talked about was her ex.

I think it has to do with showing that they have been deemed attractive or desirable some time in the past.

I’d say it’s specific to some men and an equal number of women. I’ve never done that, and I am a man.

I like @zencelo’s answer above though.

Some men never “get over” some women and vice versa. I believe it can be obsession beyond the control of plenty of people and is more common than those both afflicted and immune realize or understand.

If one doesn’t learn from past mistakes, they may be doomed to repeat them. A man or woman who talks about it just wants people to know what he/she has leaned and how it now applies. Nothing to be concerned about.

They are not worth it.
Triangulation is a go to technique for many sociopaths.

If it happens again, ask the guy why he is telling you about an ex. Unless a sired child is involved, I see no point.

Possibly to let you know what a catch he is?
Its a game that some play which could backfire on him.
Example: the women tells him to leave, or leaves herself..no more communication until he grows up perhaps.
Another reason possibly is that by confiding in you he wishes you to tell him your experiences.
( keep it too yourself until trust is EARNED between the two of you.)
Men seem to compare themselves to your past lovers.

You know what really makes me think a lot!, of how can you even know or tell if a man does this because he dwells on the past with this person ( like the what if) or if he really does it to just make you feel less, insecure, jealous, because he wants to appear important and as an interesting person.

I also think some people when they do this, they create a big story that is not even half real,
they poof it up and amplified it, especially when they want to make the other party jealous/insecure.

I dated a guy for two years that often talked about an ex-girlfriend. They had dated for six years, so it was understandable, up to a certain point. I finally had enough and said that he should back together with her. Our relationship split.

I suspect that he tracked down the ex and they married. Their names are too uncommon to be paired in an internet search. Anyway, I hope it worked out. It was clear that he still loved her and probably only liked me.

The man I found is a perfect match. Had I married the other boy, I would have been miserable.