Kind of a wall of text, my brother who is older than me. Was in a relationship with this girl that lasted roughly ~10 years, I don't really know but whatever. One day he moved out from our parents home to live alone and when he had to move again, due to the place he was staying at, evicted its tenants for whatever reason, he decided to instantly get married and move with his SO. We are talking around a 6 month timespan. So that happens, we found it he was getting married like the week before it was going to happen.

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At the wedding I saw him cry when saying his vow, that was when my red flag appeared. He cried, she didn't. I don't think she felt any perceivable emotion. During the wedding I was having a chat with some folks and they told me how he before meeting her, he was living life, but that he also lacked direction. Something the wife brought with her. She basically toned him down and from what I gather, them getting married so quickly, as well as moving in, was her idea. Even more, her parents moved in to live with them. My bro justified it as her parents helping with the rent, they bought a big house. But my parents were never invited to visit their house, I came and it was always a mess, apparently no one including the parents helped with the maintenance of the house. Furthermore the wifes side of the family regularly visited their house, I was invited too, but my parents were unofficially banned from visiting. I always assumed it was because their house was a mess and my parents would judge them for it, but i paid no mind. I didn't particularly like or dislike my bro's wife, but i respected his decision. So i did my best to get along with her, however as time went on by I started seeing more cracks. Like how they would argue more in front of me, how she was unsatisfied with his hobbies and habits, how he would talk up her getting promotions and how her job was going places, while his seem to either stagnate or get worse, at least emotionally and psychologically for him.

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The final red flags finally came through when the 3 of us were hanging out and she was shopping for a work party, eagerly, that he wasn't invited too. So the whole time it was just me and my bro talking about things, while she spent the entire time shopping, not including him with anything. A couple months down the line he tells me they have been seeing couple counselling for a while and that he was making the effort to make things work, while she wasn't. He's also been seeing a therapist about the toil this is taking on his psyche. Finally he asked her if they could make things work, she said they couldn't. They divi up all their finances, funny part is while they were together he bought all the furniture's and they included all his finances before the marriage in the split, while she remained largely unaffected. She also got the house and cash, while he got furniture, some stock and his car.

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So I chill with my bro whenever I can and we talk about things, when we went on a trip he tells me about an event that happened with his ex-wife while they were vacationing in an area they had planned to go together, but now they are visiting separately. Apparently she lost all her shit somehow, called him up knowing he was in the area. He came and helped her look for her stuff, gave her 1000 dollars of his own fucking money to help her and wanted to get back on his trip. And she berated him for being selfish, not being concerned with her losses and blaming him for this being the reason why they broke up. He also tells me on the trip, that he's been trying to get a divorce happening, but she hasn't signed it or whatever, keeping him shackled through contracts.

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Needless to say this experience has made me very wary of marriages, unintentionally racist towards her race and kinsmen and just distrustful of women in general. I also have this unshakeable resentment towards 'weak men' and people like him, so he's been divorced for say 3 years now and he's still kind of trying to find his place. I definitely think individually he's improved, both physically and somewhat psychologically, but he's just doing whatever wants, going around the world with no plans, no financial security for once he has to retire and it makes me wonder if I should tell him to settle down.

Not settle down with a woman persay, but settle down in life. Maybe it's my lack of experience and understanding speaking, but I feel like he should at least find financial stability for once he retires, like work/study and focus on career to have a house in time, otherwise what will his plan be once his reaches 60?

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Am i being overthinking things and I should just let him live life, his nearing 35-ish and he's spending all his finances travelling. Or should I really have a heart to heart with him, next time i see him?