I have seen that it truly brings my parents joy to give to their children. My mom gets true pleasure from buying me a sweater. It used to bother me because I don't need a sweater (I can buy my own, and already have more than enough), but she'd insist on taking me shopping and would get truly dejected if I didn't find anything. Sometimes, she would find something in a store she liked but comment that she wouldn't buy it for herself unless I found something, too. On more than one occasion, I suddenly "remembered" that my workhorse navy t-shirt was looking worn and, Oh look, they have navy tees and they are 50% off!, or similar. As I said, it used to bother me because I can certainly afford my own clothes, and often times these were things I not only didn't need, but sometimes barely wanted. But once I realized how much genuine pleasure she got from this, it stopped bothering me and I am much better at playing along. I still try to be very frugal about what I pick out, but I pick it out with enthusiasm. I also show enthusiasm when opening a gift that I may not need, and may never even wear, because that is my gift back to her.
My parents are in their late 70s. Very healthy and active for their ages, but none the less the numbers are getting larger than I'd like. The last few years, they have given us larger and larger checks for Christmas. They can certainly afford it and it makes them happy. I generally tell my mom that I just spent some of the Christmas money on X thing, even if it is something I would have bought anyway, to help prolong her joy in the gift. Even just, "I sent off a check to fund some of my IRA for the year, using some of that Christmas money!" thrills her. Just this week I commented that I sent out the rent payment but thanks to their check, it felt like I wasn't paying rent this month, and that delighted her.
They also offer to take us on an essentially all-expenses paid vacation most year. Most of the time, we are unable to go, but when we are able, we try to. Again, they love sharing the experience with us, having dinner with us every night, sharing cocktails at a beachside bar, etc. So yes, it is a gift to us, but they get perhaps even more out of it than we do. (If we offered to pay to take them on a trip, they wouldn't hear of it. We can't even pick up the check for dinner, though they do accept a thank you gift for the vacations, which is often us paying for a massage for mom or for an excursion for the group. If I said I wanted to use the money they gave us to make memories so how about we all go on this cruise I've found, they would almost certainly either say no, or buy the cruise for everyone.)
My sister still gets annoyed. I've tried to explain to her that finding a few things in a store that she will wear, even if she doesn't need them or feel wildly in love, makes mom happy and she should just play along. especially because if we don't pick things out, mom buys stuff on her own, and that can be even worse. I'll pick something that I at least kind like; mom sometimes misses the mark. But sister can't bring herself to do that, or to act enthusiastic with whatever gift shows up. I wish she would because it really does make mom (and dad) happy to see us ohhh and ahhh over the PJs they got us for Christmas.
They should be spending their money on things that bring them happiness. But being generally frugal, buying stuff doesn't bring them much happiness in most cases. Buying it for their children seems to, as does taking their children on vacation. And so too does leaving their children very large sums of money. So I look at all these things not as them spending money on a sweater for me or plan tickets for me and my spouse, but as them buying themselves the experience of feeling like they have taken care of their children, made their children happy and secure, and setting their children up to never ever worry about money. When you frame it like that, I think it becomes much more palatable.
I'm visiting them in a couple weeks. Mom will no doubt want to go shopping. And I will go out of my way to find at least 1 or 2 things about which I can either be or act enthusiastic, and that are fairly moderately priced. (They could afford whatever I picked. I once saw a handbag in the window of a store in an outlet mall and expressed genuine enthusiasm for it, and I was actually looking for a new handbag. We went in... and the bag was $1400! Mom actually tried to talk me in to it. This is a woman who likely has never spend more than $50 on a purse, but she wanted to spend $1400 on one for me, and certainly could afford to do so without even noticing the expense. I had to talk her out of it.) My mom will remember the day we went shopping for weeks, or longer, with smiles and satisfaction. Why would I deprive her of that, just because my pride tells me I can afford my own navy tee and my practicality says I don't need another sweater?
Letting them give these gifts to me, and being enthusiastic about it, is the gift I give back to them. Because it really does make them happier than just about anything else they might choose to spend it on.
(If money were in any way an issue for them, my answers might be different, but they are very, very secure. Also, they have never once used the money or their generosity as a weapon or bargaining tool.)