It's definitely not too serious. The man needs underwear and is obviously not going to get them on his own. He'll probably appreciate it. One less thing he has to do.
Buying underwear is only tricky territory when it comes to women. And generally only if you're not sleeping with her yet. You all will view the purchase of underwear as a ploy to get into your undies - which it is - and will make sure to comment that we shouldn't expect anything. Guys are just like, "cool, thanks. I needed some new underwear."
More simply, buying drawz for a man is just a nice gesture that doesn't imply or insinuate anything. Buying drawz for a woman is a mischevious act that needs to be commented on and clarified as to ensure that nobody gets the wrong idea.
If you want to buy him some undies. Go on ahead and do it. Holey drawz are a bad look on anybody and need to be remedied posthaste.
OMG! The guy I was seeing awhile back had hideous underwear. Big @$$ baggy holey thang. I put them on one time to run to the bathroom & he poked fun of me. I blurted out that they look like a friggin nasty sack. The next time we were together he had new boxer briefs on. I should have bought him some, but I didn’t want to offend him. Gulp…
I was in a similar situation. My guy was low on cash, and he had a pair or 2 of underwear that looked like Swiss cheese, and another pair or 2 that were starting to get holes as well. (He also never had enough decent boxers to make it between laundry days, but I think that had more to do with how infrequently he did laundry.) My suggestion to you is to ask him to be very specific about what he prefers before you buy him undies - not just whether he likes boxers or briefs, but knit or woven, solid or patterned, and if you're really nice whether he has a favorite brand. These little things matter - for example, my guy liked knits and for some reason had a hard time getting wovens over his big butt, as I discovered to my chagrin when I bought him some wovens.
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