A
female
age
36-40,
anonymous
writes:I was invited on vacation with my boyfriend and his extended family a few months ago. Since we went during the spring break, it was more expensive than I could afford so he offered to pay (not loan) the balance, which was a little under 500$.He makes a lot more money than I do and at the time, he could afford it, so I gratefully accepted because it was the difference between me going or missing out.Right now he's drowning in bills and dipping into his savings. I know he can pay it all if he's a bit frugal and curbs his spending but I'd like to help him out.How can I pay him back without offending him? How can I convince him to somehow accept the money?Thanks in advance!
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male
reader, Fatherly Advice  +, writes (10 October 2012):
 Some people have a lot of trouble accepting gifts. And I thought at first this was your problem. I see now that it is more complicated, but basically the same problem. The Real Man Code says he can not ask your for money even as the return of his gift. His savings are now paying for his decision to be generous in the past. He probably expected that, unless he really does have some trouble handling money. The best option for you is not to "repay" him but to give him a gift. In the same way he gave you a gift. This allows you to be gracious in receiving and generous in giving as etiquette requires. It offers him the same opportunity, if he is smart enough to see it before his male pride veto's it. The trick to getting around his ego / pride is to make your gifts save him money instead of giving him money. Also harder for him to turn down.
Here are some examples you could try. If you date regularly, you plan a date and pay for it. He will have that much more to catch up his bills.
If he always drives, swipe your card when he fills up. Just tell him it is your turn.
If you cook together, buy the groceries yourself before you meet. Buy extras so his pantry will be stocked.
All in all your thinking is right. The proper thing for you to do is to help him out as much as your budget allows. You are also right that it will be difficult and hurtful just to write him a check. You need to put it in terms of a gift rather than a payback. Keeping accounts in a relationship puts a separation between you. The goal is to get the relationship to the point where you can share assets intimately. Until you are "us" instead of "him and me", be open with your gifts.
I'm guessing that he needs to be supported and encouraged to be frugal in his spending. Your support in that is the best gift you can give him. Accept and encourage cheaper dates, without reducing your affection or attention to him. Home dates encourage intimacy in all areas, thus building the relationship. Remind him that you value the time together more than him proving how good of a time he can show you.
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