Here's the deal... I have a friend at work who I think is super awesome and smart and talented.  Her boyfriend, however, appears to be none of these things.  I consider her my friend, and we do hang out outside of work sometimes, but I wouldn't say we're very close.  Some of my other coworkers and I have discussed what an ass her boyfriend is.  He works for the same company but in another department. He seems to be one of those people who has no real talent or interests of his own and so just criticizes all of his girlfriend's considerable talent.  Whenever I see them together, he's putting down a project she's worked really hard on, or undermining her job by suggesting she do something a different way, even though he doesn't know what he's talking about. 

 I really think she's way too good for this guy, but I'm not sure how/if I should say anything to her.  She's in her early-ish 20s, and I think she's been dating this guy since high school.  I don't want to stick my nose where it doesn't belong, but I'm afraid she'll end up with this guy by default because she's too timid to break up with him and find someone better or be by herself.  She's a very cute and funny person, and I think she deserves better.  Should I say something or just let things take their course?
Concerned Coworker

If you are actually friends with this woman, then I suppose there is no harm in simply stating your opinion. Maybe she is just insecure and no one has ever told her how great and smart and talented she is, so she stays with this jerkface out of habit or fear of being alone. The thing is, you are obviously into her, so if you say these things with the expectation that she will leave him for you, you may be making a huge mistake. She may think you’re being really nice, and she may even take your advice and ditch him. Thing is, she might just think that you should mind your own damned business and stop insulting the man she loves. 

If you are willing to take the risk, then go for it. But you may lose her friendship if you do. On the other hand, being around people who don’t treat her like crap might have her coming to her own conclusions about what she deserves and what real relationships are like. You’ve heard the phrase “Show, don’t tell”? Maybe you can just show her how non-assholes behave and she’ll come around on her own.

So, my buddy started seeing this girl a few months ago. At first, I didn’t think much of it because he never really gets too serious about girls and dating and stuff. I have known this girl for a long time, we come from the same hometown, and she used to date one of my brother’s friends back at home. Well, she’s kind of a slut. She got a bad reputation early on, and it seems like she just kind of decided to go whole hog and throw it in everybody’s face, so she just kind of jumped from guy to guy for a couple years. Granted, this was several years ago. We’re all in our late 20s now, but still. 

So, they started hanging out, and he mentioned that she was from my hometown and asked if I knew her; I said I did, but not that well. Like I said, I didn’t think it made much difference because I thought he’d get bored with her after a few dates, but he didn’t. Also I’m not the type of guy to go spreading gossip from that long ago. Thing is, when she dated my brother’s friend, she cheated on him and then she got engaged to the guy she left him for. I guess they never got married, but I know she cheated on that guy, too. 

So, now my good buddy is dating her and he seems like he is actually pretty serious about it, like calling her his girlfriend and saying stuff like “I think I could actually get to know this girl.” This may sound ridiculous to you, but that’s about as serious as I have ever heard him talk. He’s always going out with different girls, but never for long. There are plenty of my friends who have tried to be his girlfriend, and he always blows them off. So, I guess I’m worried that he might actually get hurt here. And if he finds out what I know and finds out that I didn’t tell him, he will probably be really pissed at me. What should I do? I really don’t want to get involved, but I don’t want to be an asshole to him either. 

On the Fence

I think you should let it go. Like you said, her reputation was built a long time ago, and you don’t know what she is like now. In fact, it’s likely that half of the escapades you heard about are total bullshit anyway. And if not, then perhaps a reformed slut is just the medicine your slutty friend needs? (I note that you never used that word to describe him, though the behavior you describe certainly seems to merit the label. I’m not gonna go all batshit feminist on you, because you seem like a nice enough guy, but please think on that for a minute, won’t you?) 

You can’t assume that her behavior from over a decade ago reflects the person she is today. If you’re worried, you can always have a private chat with her. I’m sure she is aware that you must know of her former reputation. She will probably be grateful to you for not gossiping to your friend, and you can let her know that as long as her intentions are good, you’ll keep your mouth shut.