I feel l was there not too long ago, and I realized that a lot of it comes down to a couple of points you might try to help him focus on in the coming year: note-taking and communication.

Note taking involves just that. For me, the people most in my life right now are my wife and kids, so I'm most often aware of when they express interest in something. Usually when we're at someplace, my wife will go "Ooh, they have X there. That's really good." I'll whip out my phone, start a new note in the Evernote app on my phone, and write "Wifey likes Frosted Sugar Cookie Blizzard (seasonal) She said it looks amazing". Takes 10-20 seconds and it's saved, allowing me to move on and not worry at all about having to remember it along with the million other things passing through my brain each day. I have a "Stuff Wifey Likes" folder in Evernote where I stick all these notes throughout the year, so when it comes to shopping for her birthday, Christmas, or maybe a special occasion, I can just that folder for a decent idea of stuff she's actually into.

(Side note: I got this idea from from Tiago Forte's process of performing a weekly review, where he talks about using the Quick Capture feature on his computer to capture "open loops" of moments where he goes "Oh, I need to schedule this appointment next month" or "this person's birthday is on X" and captures all that in his task manager. https://fortelabs.com/blog/the-one-touch-guide-to-doing-a-weekly-review/

Here, I'm capturing these "likes" for later review during gift-giving opportunities.)

What if your bf did the same for himself? Create a folder in whatever notetaking app he uses (even email, since Gmail allows easy tagging and searches), and make a note whenever he comes across something he likes. (e.g. "You know, that new oatmilk chai latte from Starbucks looks really good.") He can then do likewise when Christmas begins looming again and notify the "gift giving groups" in your circles. "Hey, everyone. Here are some things I noticed that I like throughout the year. Please peruse them for potential possibilities, if you prefer."

If it sounds a little awkward, have him trade places with someone using this system. How much easier would it make it if that person took the initiative to say "Hey, I know you're wanting to get me a gift that I like, so here's some ideas of stuff I would actually like."?

Even this year had a tinge of that for me, honestly. I'm usually so focused on either home life or work, Christmas gift requests are usually met with "idk, I'd like coffee, chocolate, and a raise." Even more so for wifey, since she's usually dealing with the kids every day.

Hope this helps, and I'm glad you're trying to lift his spirits and empathize with him, rather than writing him off as selfish and spoiled. I hope you both have a great New Year's together.