I am a 47-year-old gay man, healthy, in good shape, told I'm attractive. I have been dating a man in his late thirties. People have told me that the age difference is not very apparent, and it doesn't seem to make any difference anyway. I think we are a realistic couple; he is attractive but not so gorgeous that he is out of my league. I make more money than he does, but that's no problem. Now and then I'll pick up a check; he does not encourage it. Just a while ago he asked me to move in with him to his house -- we would be a couple -- but it seems there was a stipulation. He told me that the house needed many repairs, some cosmetic, some not, and asked me to pay for them, his rationale being that this would be my home, too, and that if by any chance I should outlive him the house would become mine, as he was leaving it to me in my will. None of this sounds all that unreasonable but I confess I was a little put out. I hadn't even made up my mind to move in and already he's asking me to put in a significant amount of money into the house, many thousands of dollars. I can afford it, but I'm worried. It just makes me feel that maybe my being a little well-off as compared to him is what really matters to him. I should say that he works, has some money in the bank, and our sex life is more than adequate. Maybe I'm just lonely ... what do you think? He also wants to go to a bear meet but indicated that I would have to pay for both of us.
Paying for home repairs when you're just embarking on a committed relationship [after dating for a short while, I imagine?] is a little sticky, especially if most of the problems are merely cosmetic. It is possible he sees you paying for the repairs as a substitute for rent -- you didn't mention it, but lovers rarely are required to pay rent if their partner already lives in a house. Also, he has to pay property taxes on the house, and he may see this as your way of paying your share. [Remind him that fixing up the house will increase the property taxes!]
If your boyfriend is guilty of anything, it's lousy timing. I can well understand why he's got you questioning his motives. What does he want -- a lover, or someone footing the bills? You better sit him down and ask him just what he expects from you. Is he implying or outright stating that you can't move in unless you pay for repairs? Romantic little devil, isn't he?
On the other hand, he does have a point that it will become your home [if not your legal property] once you move in. The whole business with leaving it to you in his will is kind of moot since no one knows at this point who will outlive the other, but it's something.
I think the real problem is that you've haven't made a full commitment to this guy in your heart. Why should you pay "many thousands" of dollars for home improvement if you wind up splitting up with the guy and moving out in a matter of months? Is he willing to pay you back if things don't work out?
I hate to resort to cliches, but as they say, you never know someone until you live with him. Tell him you need a period of adjustment before you can give him a definite answer about the money. It's not that you won't do it, but you have to see how it feels living with him, in this strange house [and, presumably, a different neighborhood?] and so on. There are just so many variables and unknowns -- for both of you.
But handle this delicately. He may be a perfectly nice guy and the two of you might make a damn good fit, both in and out of bed. Just explain that he's being just a little premature. If he's really in love with you he'll be willing to wait. Move in with him if you want, and see what happens. Offer to pay some rent in the meantime so he doesn't think you just want a free place to live!
As for paying for the bear meet, that could also run into significant money, but it's also true that he may not be able to afford it, and equally true that it will be less fun without him -- make it a loan instead with no hurry to pay it back and see how he reacts. You can always forgive the debt if things work out and sue him for it if it doesn't, LOL.