Will he ever change?

[Midthirtiesdatinglife]

I’m recently divorced and in my mid thirties with no children (i would love to have children) I have been in a relationship with a man I knew from school for the past 6 months. He is 41 and has been split from his wife for 3 years and they have a 9 year old daughter who is lovely and sweet. His parents are extremely wealthy and he has been living at home for the past three years since the split. They also bought him his car and he doesn’t have a stable job. I have my own house and a very good job and I feel like I am dating someone who doesn’t have their financial or physical shit together. He doesn’t really make any plans for us, he is just always waiting around for me to suggest something or to finish work. What should I do? He is a lovely person so I don’t want to hurt him.

As they say the best indicator of future behaviour is past behaviour. Getting into a relationship with someone on the basis that they'll change is, I think, a hiding to nowhere. He's 41, if he were going to pull his socks up he'd have done it by now.

Has he always been like this? Did he have his shit together before his first marriage broke down? Or do you the way he is contributed to his marriage breaking down. If it’s the former he might be able to get back to where he was so you could talk to him and find out why that’s not happening for him and see if he needs any support to get back on his feet. If he’s always been like this, with no get up and go, he’s unlikely to change.

It doesn’t sound promising OP. Stop worrying about hurting him - he’ll be fine…! He’s well supported isn’t he?! Make the choice that works for you. Sounds like you want someone stable and independent like you. I would want the same.

@ShillyShallySherbet I have been trying to figure that out. I don’t think he has ever owned his own car, they have always been bought for him by his Dad. I don’t think he has ever owned his own house (there have been a few white lies around this at the beginning when he said he gave her the house - but I have since found out that the house was rented). The biggest flag for me is that he has had the best in private education, no bills to pay even down to car insurance. He smokes, but doesn’t buy new clothes or go on holidays. I left my marriage with nothing and a menial job but managed to pick myself back up because I had to. I worked so hard to put a roof over mine and my dogs (lol) head because I had no other choice.

Sounds like he’s had everything handed to him on a plate. Has he ever had a decent job? He doesn’t sound like he’s ever grown up. You would be well within your rights to walk away from him and he’ll either just carry on the way he is living the cushy life or it’ll give him the push to become more self sufficient and grow up.