Do I wait for him to propose?

Thank you for the added information — and for the kind words. 😀

There are a couple of flashing yellow lights in the information you added based on my questions, and then I guess the questions got you thinking because the additional information you added that I didn’t ask for also began to paint a picture of a man who isn’t marriage minded. I think your instinct to give yourself a time limit with him and in the meanwhile to start building a support system for yourself to get back out there is a good one. Follow it!

I take it he’s about your age, 38, and has never been married. This is a flashing yellow. It sounds like marriage isn’t on his personal radar. It’s more like something he has to give up in order to keep you. Ideally marriage is something you both want. There are enough differences in relationships where couples have to compromise and make deals — marriage itself is too big an issue to be a deal making tool.

While it’s great that he has a job and is working to pay off his debts, and is living with his father in the meantime, the fact that he’s been living with his father for two years and is probably going to be there for a while more, means he isn’t ready to get married. If you had come to me when you first started dating him and asked if I thought he was appropriate, I would have told you to find someone who is more ready to be in a serious relationship. Anyone who’s living with a parent in their late 30s or early 40s, isn’t. Because you’re 38 and have two kids, you have to be especially careful with your time and emotions. You need to date men who are more compatible with you and if you know what you want (marriage in this case), then you need to choose someone who’s ready and willing. Not only is this guy not the marrying type he’s not financially ready and he’s living with his dad.

One of the things I talk about in Think & Date Like A Man, [url]http://www.askapril.com/relationship-dating-advice/think-and-date-like-a-man.html[/url], is that you have to treat dating like you would a business. I know you think he’s nice and kind he helps you around the house, but that’s just part of the picture. You need to look for someone who’s financially ready to get married and who is socially ready, too. This means someone with a good job, manageable debts if any, and a working relationship with his ex and his children so that blending families will actually work! When you get too invested in someone who doesn’t have enough of the attributes that will make him a good match for you, it’s hard to see what’s wrong because you’re emotionally, sexually, time and family invested in him. Now, breaking up takes on a value, too. 😕

You’ve hit a wall with him, and because he’s not stepping up to the plate, you’re turning into someone you don’t want to be (I can hear your frustration when you say you’ve had “The Talk” with him about marriage multiple times.) because you can’t get him to be who you want him to be. This isn’t a productive or healthy dynamic. Instead of trying to get him to be someone he isn’t, I encourage you to accept who he is. And that’s a guy with some wonderful qualities….. who isn’t your Mr. Right. In fact, I think the reason you find the relationship to be cooling off is because he realizes he can’t be your Mr. Right, and that’s not an attractive feeling for a man. 😳

You’ve invested 14 months in him, as a 38 year old divorcee with two kids. He hasn’t stepped up, and it’s time for you to move on. You can give yourself the three month deadline, but I don’t think he’s going to change. The question is, will you? I know you say you don’t have the guts to start dating, but if you give him up because he’s not going to be the right man for you, and you find yourself single, I think you will. 😉

Please let me know how things go for you, and please follow me @AskAprilcom on Twitter and on Facebook at this link: [url]https://www.facebook.com/Relationship.Expert.April.Masini[/url]. 😀