Dear Jellybean,
I'm in a serious relationship with this guy that I was previously best friends with for a year. He's number one in my life, but lately his jokes and comments to people have been annoying my girlfriends.
He's a person who likes to harshly joke around with the girls and likes to make fun of them, about their appearance or actions, and they all know he doesn't mean harm and has good intentions. He is good friends with most of my girlfriends, but whenever he starts off with the jokes, they get really irritated and start attacking him all at once, and also get me involved in it; telling me to "teach him how to respect them."
I love my girlfriends too, but I really don't know who to side with when those situations occur, do I defend my boyfriend saying he doesn't mean harm? Or should I side with the girls and tell my boyfriend off? It's really confusing because I know my boyfriend wouldn't change his habits because that's the way he just is, it's in his nature to joke around with everybody. I tried telling him to ignore them sometimes but we are constantly around them in break-times and classes, so it becomes akward all the time. What should I do? I feel bad if i don't take sides and just sit there and do nothing about it, and it's hard telling both sides to stop attacking each other because they wouldn't listen.
-Stuck in between
Dear Stuck in between,
I respect the fact that you care about this guy, and have spent a year of your life in a friendship/relationship with him. But I have to tell you, everything you said in your letter makes me think your boyfriend is - um - a big jerk.
A guy who tears women (in particular) down with jokes/comments about their appearance and actions, is a guy who doesn't like women. Maybe he's intimidated by girls, or maybe he believes that females are inferior to men. But whatever the cause, your boyfriend is acting very offensively, and if he can't change his habits, I seriously suggest that you change boyfriends.
It's one thing to be a jokey kind of person, who gently teases his friends and acquaintances. But it's quite another thing to be someone who walks around offending half the population. If your boyfriend doesn't change his habits, not only is he going to end up alienating a lot of people at school, but he could grow up into a bitter man who has trouble getting a job (if his interviewer happens to be a woman) or making adult friends (grown-ups don't put up with this kind of crap).
I'd be shocked if some of this behavior isn't happening in your relationship too. Does your boyfriend take pains to point out your flaws, or laugh at you when you make a mistake? Is he convinced that his opinions about music, politics, and other subjects are "right" - and that yours are "wrong" if you differ with him? Does he show up late, not call when he promised to, or do other things that show a disrespect for your time and feelings? All of these are ways that men who don't like women will commonly disrespect us. Ask yourself seriously whether your boyfriend is treating you the way you deserve - or whether you've been putting up with less than stellar treatment, because you like having a boyfriend.
If you really love this guy, and want to keep him as a boyfriend, tell him he's got a choice to make. He can either start treating your friends with respect, or lose you as a girlfriend. That makes it his decision - and the choice he makes will tell you, for certain, whether he is worth keeping.