I haven't checked with my accountant yet, but I've been to two fundraisers at bars recently, and I'm pretty sure that I can write these things off. Whenever I get an e-mail from a co-worker or relative asking for a donation to sponsor their fundraising marathon, walk or pub crawl, I always donate. Here's my strategy: I go to their fundraising website and find the lowest donation, then add $5 and donate that. I employ the same strategy with wine lists. In this case I always choose the second cheapest bottle. It works the same way -- it gets you there and makes you feel alright, and you don't look like a cheap jerk to everyone else.