Oh boy.. I think you guys definitely need to sit down and really TALK about money and what your goals are and how much you guys would want to save per month for retirement, rainy day fund, fun things fund and etc before you guys even move in together and let alone buy a house. I think an above poster had a perfect suggestion, rent out one of your houses first before selling both of them and buying one together. Also I would not be going to Atlanta if you're having to charge your groceries and your wisdom teeth procedure. I also think it's a bit odd he MAILED you the check. I'm unsure if this is a long distance relationship or what and you guys only see each other on weekends or what the case is on that but that would make me think he doesn't plan on seeing me again if a check were mailed to me by my boyfriend. And his comment to you about how he doesn't want to be punished by your debt is also a red flag to me. You yourself just said you're concerned and that he's weird with money already so it sounds like you need to listen to what your gut is telling you and maybe hold off on some of these things like buying a house together. But just have a long good talk with him and I think afterwards you'll know what to do. If he refuses to talk then that's an answer in itself.

I think Midwife says it very well.... Tough situation.. but it's best to address it now, than to continue revolving debt...

I really appreciate everyone's opinions.. I have a very open mind and agree that we HAVE to talk about this stuff.. Upon reading some responses I noticed that I kind of made myself sound irresponsible and greedy.. Not to "defend" that.. I do just wanna say that I guess I've been screwed big time in the past b/c I've always made more than the other person I've been with and always helped them out and took it on as a partnership & to benefit us both.. lets get this worked out.. type of attitude..
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and the wanting to go to atlanta when i need to charge groceries is def sounding bad.. ... I guess in my mind.. i know that i need to charge a few groceries the next couple weeks to hold me over til next pay day.. it's not that i'm starving and wanna take a cruise .. i know.. i know.. my way of justifying probably..

I guess I just think of a partnership being formed .. I take on his problems and help him work through them.. shouldn't he be doing the same.. not mailing me a check for $25 .. when we see each other everyday at work? couldn't he just have offered to pick up some groceries? Or offered to help me out with my wisdom tooth removal..

The house we are buying "together" is only going to be in his name since we are not married.. and I have already made it clear that my house will not be sold until we are engaged and moving forward.. so when he wanted to move forward with the house hunting I took that as he has a plan in the works..

I guess the bottom line is I need to talk to him.. I don't think I'm comfortable having a significant other who lives a better life than I do because he makes more than me.. I just want him to treat me like I would treat him if the roles were reversed..

Money is something I've never fought with someone about before.. but I guess that's because I'm used to having more and being generous with it..

Kudos to you for taking the responses here well - I have to admit that some of them (mine included) were strongly phrased. :)

One thing that you might consider is that he might have been burned financially before or that someone he knows or is close to might have been financially burned and so he's being more cautious than he might otherwise be. Also I do believe it's true that one can be generous without being generous with your *money* ... he may feel the same way - that he's supporting you emotionally or in other ways.

Money is a really touchy subject and it can make or break a relationship. I've been there on both sides of the equation many times.

As far as the trip to Atlanta goes - I do understand. I don't think it's a wise decision for you given what you've told us ... and given that you kind of expect help paying for the wisdom teeth ... BUT ... I will say that I've made similar decisions in the past myself (Ahem - massage package at the spa and then realized that I spent more than I thought I did and was going to have to pull money from my tax account to pay the rent??? ... no ... uh uh. Never did that.). Sometimes it takes someone on the outside to say "maybe you should think about that a bit".

I don't think he's being unreasonable. I don't think you're being unreasonable. I think you're each coming at it from different angles and need to talk about it a lot more in depth before you move in together.

I know in my own relationship - I am much more comfortable carrying debt than my husband is ... and I'll carry a few thousand dollars in debt w/out a qualm. But I hate spending piddly little amounts here and there on a daily basis. On the other hand, my husband freaks out about any kind of debt (thought he'd have a stroke when I put my new $4000 camera on my credit card) but he'll eat out every day of the week for lunch and not worry that at the end of the pay period, he's got little cash left. Different people, different worries, different perceptions. It all just has to be discussed.

Good luck!

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I dunno, as an outside observer, I see it as more as 2 people with different philosophies and way of managing their money rather than one having a better life than the other. Including the ability to live within their means.

I've known people who made $200k/year and weren't able to live within their means while others made $20k/year and were able to live within their means (and actually have savings). It sounds like you aren't able to live within your means and you are not even able to live paycheck to paycheck. I can understand 'issues' coming up but those issues are always inevitable and need to be planned for somewhat. I think we can all understand though getting caught in a bind and being a bit frustrated by it.

When I was dating, I did date guys who made less than me as well as guys that made more than me. I never really felt in either case that either of us had a better life than the other. The amount of money you make rarely has anything to do with your ability to budget and live within your means. (Of course you could be making peanuts but even people making peanuts can make do, sometimes). My husband makes more than me and did when we were dating but yet I was the one that had things that he didn't, such as a house (and a reasonable mortgage). Of course with our combined incomes, our goals are shared goals are similar to our individual goals: save money, avoid debt, plan for the future and most of all, have fun while doing it.

The real idea though is that both of you talk through the finances and establish expectations which sounds like you are on the way to doing.

i pretty much agree with the above posters. Its hard to expect someone who's finacially responsible to accept your debt/loans. I was once in your position. Had a large amount of credit debt and school loans. However, I quickly made myself turn things around. I budgeted better and didn't take trips when money was not available. I still have a student loan...and dh was definately not exactly thrilled but we made lots of agreements, budgets etc when we decided to get married. I would highly recommend to follow the suggestion of not selling your house and renting. Move in together...but before you do...straighten out all your finances. Figure out how things are going to be paid for. Who's going to pay what etc. I also think you shouldn't be going to Atlanta if you have to put groceries on a credit card. I know its probably what you don't want to hear...and i know we all need a break..but if you have to charge it and don't have the ability to pay it off at the end of the month...you shouldn't go. I think it would be wise to sit down with a debt counselor. There are many of them out there that will help you for free. It sounds like you really need to take a good look at ways you could cut out expenses and get debt under control. You should never rely on others to help you out. Finances (like others stated) are one of the biggest issues that end most relationships. You shouldn't rely on him...even if you are in love. I know its hard to get finances straighted out...but its time to really take a look at your budget and get cracking on ways to get rid of the debt. You should also seriously think about getting a good understanding of how each would contribute financially to the relationship before you guys move in together. Good luck and I hope things get better for you.