My son (age 33) has had 3 long-term relationships, 2 of them were marriages. The first time was when he was 18 and married the mother of his year-old daughter. They really tried to make it work, and lasted 5 years. He was just too young and immature, and she was not good with money and ended up in jail for 9-months because of it. They separated and divorced soon after.
His second long-term relationship lasted 3 years. She wanted to get married in the worst way, but he kept putting her off. She was abusive, both verbally and mentally, yelled all the time, was a terrible mother and he finally sent her on her way.
His third relationship ended up in marriage, after they lived together for 2 years. I thought that one would last, since they already knew each others strong points and faults as well, but sadly it did not. They were both too stubborn to do much giving and even after counseling it did not work out. He wanted to get back together with her, but she wanted to keep things as they were with him spending most nights at her place, but fixing her car, babysitting her kids, etc. He finally said that was enough and either we get back together or we split. She chose to split, and had a new boyfriend moved in even before the signatures were dry on the divorce papers.
He is looking, but in all the wrong places (mainly bars). I don't think he will ever get married again though, he's been there done that twice.