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Why is he buying gifts for his friends? Especially when he doesn't have the money? WTH?! And why would you subsidize that, especially since some of the recipients are complete strangers to you? You're enabling his over-spending.
To your greater question, it all depends on how much $$ you make, and how secure that allows you to be. If you can afford to cover all his expenses, as some higher-earners can, then there shouldn't be any worry. Depending on level of income, some wage-earners cover everything, from family expenses, to retirement savings, and kids' college fund. If you're at that level, there shouldn't be any concern.
We don't know enough about your situation to be able to advise you. We also don't know him; only you can decide if you can trust him, to create a little savings account with the amount of the rent he wouldn't be paying you. But frankly, if he's saying he wouldn't pay you the same amount he's paying for rent now on his own place, but justifies holding out on you by claiming to put the remainder into a savings account for you both, I'd back away from the guy. Sounds like he's trying to sell you on a shell game.
That, combined with the history of over-spending, impulse buying, asking you to pay for gifts to people you've never met, etc. sounds like you're in love with the wrong guy. Of course he's "very much in love" with you. You're the one with the money.
Well said.
IMHO, if he can't afford to buy gifts for his family and friends he is the one that needs to fix that not bug his girlfriend to buy them gifts. What a cheapskate! And, he probably lets his family and friends assume that he paid for those gifts.
If you think that it is bad now I suspect that it will get worse, much worse.
gifts for his family and friends some of which you've never met!
I would think this is obvious. Unless he's holding a gun to your head, if gifts need to be purchased for someone he knows that are his friends, tell him it's HIS responsibility and that you're not paying for that anymore. You should never have started paying for that in the first place! Quit being a doormat and tell him no.
IMHO, if he can't afford to buy gifts for his family and friends he is the one that needs to fix that not bug his girlfriend to buy them gifts. What a cheapskate! And, he probably lets his family and friends assume that he paid for those gifts.
If you think that it is bad now I suspect that it will get worse, much worse.
This was exactly what I was thinking. This is a two-bit guy fond of making grand gestures towards friends and family, on someone else's dime--the OP's. He makes grand generous gestures in order to mask and in his mind--compensate for, his own inadequacy and lack of discipline. IOW, he's a loser trying to appear to be a winner, on the OP's dime. This was the sense I was getting from the description provided.
Trust your own gut instincts (and that of your daughter) and do not either live with or marry this man. If he doesn't want to live separately, tell him to deal with it or find someone else who will tolerate his lack of financial responsibility.
This is especially important advice if you are financially secure and close to retirement age.
You love your bf and vice versa. He is very much in love with you but how come you feel that you're being taken advantage of sometimes in terms of money if you have a lot more than him (he's usually fairly generous but you've been paying for things that are really his responsibility like some gifts)? Because of that and because in the past he has let his impulse overspend and then come up short (and also since sometimes he admits to "being short" in terms of his bank account), you don't always trust him with money matters and due to that you are very hesitant to build a life with him.
He's hadn't been great with money and has limited funds but he has learned how to budget better.
Will these fears go away once you're living with him or not? If he's offered to pay you each month you live together but it's a lot less than he's paying in rent and then take the difference and put it away for you and him do you trust him to actually do that and also not spend that $? On the other hand, if you break it off will you always regret it?
These are grounds for relationship termination.
I get that you're in love with the guy, but you don't trust him. You feel taken advantage of.
If you and he aren't on the same page, financially, it will spell out problems later on in the future in the long-term.
You don't want to date someone who will willy nilly give your money away, gamble, or invest into not so-smart investments (scammy ones) because they aren't on par with you in terms of being fiscally savvy. You don't want to seem like you don't have faith and confidence in this person either, but there's a level of gullibility you need to weed out, because if this person can't trust your judgment and discernment on people and situations, in general, you're not going to be happy campers.
There's an enormous difference between two people being infatuated with one another and two people being in love with one another enough for a lifelong partnership. The difference between the two lies in the simple question: "Is this someone I trust implicitly?"
There are lots of people who cannot differentiate between the two. If you are with someone whom you adore but do not trust, the adoration kind of wears thin after a few months or years of one-sided relationships. We do not marry for money (At least we shouldn't), but we understand on a fundamental level whether or not someone is responsible. It is no picnic to carry a spendthrift through life no matter how adorable he or she might be. If, on the other hand, someone might not earn a lot, but takes his or her obligations to the relationship seriously, then that person is a keeper.
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WTH?! And why would you subsidize that, especially since some of the recipients are complete strangers to you? You're enabling his over-spending.