Dear 100 Hour Board,
There is a man that I am interested in dating, but who has a girlfriend. The attraction isn't only one-sided, and we've talked it through, but he sees his relationship working out therefore I promised I wouldn't bring up my feelings for him. We're still friends.
Do you think it would be inappropriate to buy him a Christmas present? And are there any specific gifts that might be inappropriate in this situation?
For additional context, if that's helpful, it's a long-distance relationship and I doubt the girlfriend knows about me. I don't want to do anything to jeopardize the relationship because I don't want to disrupt his happiness.
Oh, there are ALL SORTS of gifts that would be inappropriate in this situation: underwear; a "love mug," which apparently has its own category on Etsy (I can't guarantee that all the results on the results page will be appropriate, so click at your own risk); a stock photo of a happy family with a note that says, "I want this for us," (really anything with a note that says, "I want this for us" would probably be inappropriate); this horrifying book called When Clowns Attack (because that's an inappropriate gift for literally anybody); etc. etc. I could go on but you probably don't want me to.
But in any case, you probably knew all those things were inappropriate before I told you. If you want to get him a gift, just follow basic social norms, and stay within the bounds of your own rules for gift-giving (for example, if the most you get for anyone else only costs $5, don't spend more than $5 on him).
P.S. Speaking of inappropriate gifts, Frere Rubik shared an awesome story with me: apparently he knows someone who is a fashion designer, and at one point during an internship this fashion designer was asked to design some women's lingerie. He thought that his now wife, but then ex-girlfriend, would love it, so he had a pair sent to her in the mail WHILE SHE WAS HIS EX-GIRLFRIEND. I truly wish I knew how he recovered from that and ended up marrying this woman.
From what you've told us, there's no real way to know if it would be inappropriate. My advice is to treat him like you're treating your other friends. Are you getting them gifts as well? Are those gifts individually purchased or personalized? If you are going to be putting in more work for his gift than for the others, then I would advise against it.
Side note, girl, you gotta get over him. You aren't doing yourself any good by worrying about this so much. I know that it's hard to let go of someone, but starting to let go sooner rather than later will be better for you both. I'm sorry if this sounds a little harsh, but I think it's a truth you have to face.