"Okay, this is weird, but my boyfriend's facial hair is really...prickly. It actually hurts me. How can I tell him to fix this without being overbearing or hurting his feelings? Is there some kind of beard conditioner he needs to be using?"
I don't know much about beards, but I do know there are tons of small-batch (and corporate vat), man's man, facial-hair styling and cleaning products out there made with love and vegan bacon and lotion. This one has a skeleton pirate on it, so I'd say we found the winner. Why not splurge on a small bottle? Also, if his feelings would get hurt by you telling him that his beard is prickly, maybe he shouldn't be rocking a beard in the first place. No shots, just saying.
"I really want my boyfriend to have a well-tailored suit. There are plenty of occasions in his life where it would make sense, and he would look so good. Help me convince him that this is a purchase worth investing in!"
Every man deserves the right to look strong and respectable and feel fly. A well-made suit that fits properly (not too tight, hipster dudes!) will be a game changer for him, especially once he sees how versatile a two button, notched lapel, gray or navy suit can be. You don't even need to sell him hard on the "your kids will wear this" tip, just explain that one beautiful piece will be less expensive than three cheapo ones in the long run and that it's the quickest way to gain respectability and that he looks sexy in it. Have him drop me a line @iamaronow with any questions, happy to help.
"I did something embarrassing in front of a guy that I like and his friend with whom I have a decent relationship and see fairly often. I'm working it out with the guy, but I'm not sure what the etiquette is with his friend. Will it make it worse if I reach out to him and say sorry?"
This one is very difficult to call, given the lack of specifics. If the dude's friend is someone you plan to have a friendly relationship with, then I'd say you should find a subtle way to apologize or acknowledge you were out of line. Maybe not a formal email, but you can bring it up next time y'all are chilling on some real "oh boy Cindy had a wild night"-type steez. Also, what did you do?! I hope we don't have to throw you in etiquette jail!