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This is really troubling. I don't see you as judgy/bitchy. I understand your concern after reading this. On what basis are you thinking he will right things quickly once school is finished? IDK, Cresc. I have a bad feeling about this.

It gives me a bad feeling too, but then he has been supporting himself just fine until I came along. He has work experience in the field he is pursuing his degree in (CIS, systems securities), and he has a lot of connections through friends and the military. His expenses aren't that great, and he isn't a big spender. Perhaps I make it sound dire since he is currently spending more than he is bringing in, but even a part time job would fix this. Once he starts working he should be quite comfortable. It's just a matter of will he want to and how hard will he try.

Sean, the thing I am struggling with as far as a come to Jesus, he is an adult and we aren't married. If he is comfortable scraping by and not planning for the future/emergencies, that is his choice, even if I don't agree with it. I can't insist he get a job for fun money and savings if he is pulling his weight on joint bills and not asking me to pay more than my share.

ETA: He has said he wants/needs a job, but I can't be the one to flip the switch between, oh it would be nice, and active pursuit.

[This message edited by Crescita at 4:19 PM, October 4th (Friday)]

This is just me, but, nah, I do not wish to go all in again, and I'm fine with that.

No, going all in before wasn't worth it at all, to me, IMO.

I've been thinking a lot these past few days about this question, but haven't had time to post.

Before you gave background, my comment was going to be something along the lines of I will go all in emotionally, but not financially. I've already supported someone once, and I won't do it again. If I get serious with someone, he must have decent retirement savings, a salary close enough to mine that it won't preclude us from doing things (or me having to pay for everything and resent it) and our financial philosophies must match.

I don't know -- a lot of what you write is pretty red-flaggish if you see a real future with this guy, and your further explanation sounds like a lot of making excuses to explain away something that bothers you. Of course, that's me sitting here on the outside. But cashing in retirement is such a HUGE financial set-back. And, it would be one thing if he were going to school full-time and working a part-time job, but the way you describe his recent actions makes me think that you're seeing the real him after a couple of years (in terms of his work ethic) which could cause major problems if you see a future together. That type of personality trait is usually pervasive and not something that really changes.

But I could be full of beans! Definitely trust your gut and communicate!!!

Well we talked this weekend and made some ground. He understands my hesitation, and how it is difficult for me to judge his character when half of our dating life has been him acting out of character. Even outside of our relationship, he knows it is a path he can’t continue and he will start working harder to remedy the situation before he graduates.

I’m still at wait and see, but at least he knows how I feel about things.

I'm glad you had that talk. The two of you are learning a lot about each other now. But when someone begins cashing out retirement funds like that without true hardship it doesn't makes sense. Regardless if he can still pay his bills, etc it's still a refection on him of what you think of him...KWIM? It doesn't make the case for you WANTING a future with him and he needs to see that. I think the majority of women, whom have careers or not, want a guy who is a go getter. Who has good future financial prospects and can make them feel safe. I think it's just part of female instincts to want and look for that in a guy. And I see nothing wrong with it.