Buh-bye Brian, hello new guy!
Sorry, but your old boyfriend is not mature enough to be serious boyfriend material let alone husband material. He has too many problems being a man to be a partner to a healthy woman. I hope you are able to value yourself as a prize, enough so that you’ll give a man something to chase and win (you!). Men feel much better about themselves when they feel like they’re providing for their woman and that they can go out into the world and slay dragons.
Brian is very needy and he’s not standing on his own two feet in terms of job and career, which are crucial to a man’s self esteem. Down the road (and perhaps very soon) you may very well end up resenting all the work you’re doing for him, and you may be surprised to find he’s going to feel depressed and angry at himself for not being better able to take care of you. The truth is that you’re acting like the guy in the relationship and he’s acting like the woman. Stop rescuing him. Quit driving 40 miles each way to see this guy. Sheesh! And listen to your family — they’re right to be wary of him because of his job status. At 28, he should have a job and be building a career.
I am very sure you are ripe to read my book, Think & Date Like A Man. You can purchase it by clicking on the Dating Advice Books link above. It will give you a step by step plan to be your best self and find your best romantic partner. You should really read it now. In fact, read it before you go out on any more dates with this new guy. It will help you date better in the future.
This new guy sounds really great, and your own doubts about Brian make it clear to me that you’re ready to move on. It’s truly in your best interest.