How can I both be a good friend and stand by what I believe in at the same time?

By realizing that she's not you, that you're not even really involved in this situation so what you would do or what you believe don't really enter into it, and that you can support her without 100% agreeing with everything she ever does. If we only offer support and friendship when we agree 100% with what someone else does, we're never really going to be there for our friends.

People make mistakes. People do stuff you wouldn't do. That doesn't make them bad people, or unworthy of love.

I agree with occiblu to a point.

There are two sets of boundary issues here. The first being that you likely would not behave like your roommate, when she violated her bf's email account (although if I have a guessable password, I am likely a fool).

The second issue is that, as occi says, you are not her. She needs support, but support from a standpoint of "I would not have done what you did, but I still understand that it sucks for you."

I had a best friend once, and I saw her bf and HIS ex gf at the river one time. He went ahead and told her about this rendevous, assuming that I would tell her. She was furious at me for not telling her but there is on way in hell that I ever would, esp. since I was friends also with the bf. I was offended that he even assumed I would spill the beans. This was years ago and I guess it still bothers me.

Good luck. I think you can do this, be a friend and also be true to your beliefs at the same time. If she does not want to hear that, her prob.

Thanks, occhiblu and danf. I've stood by my friends through things that I've disagreed with before, but violating someone's privacy is a very big deal with me. And it'll be hard for me to say things like "He's an asshole," even if I agree that he is. We'll be drinking a lot tonight, so maybe the beer will help me be less judgmental. Or maybe it will have the opposite effect. I really want to try to be nice and comfort her tonight.

She certainly didn't act very honorably, but neither did he.

Is it possible for you to allow their respective dishonors to be their own problem and just be a supportive friend? He's the one who has the beef with the way she found the information. As repugnant as her actions are to you (and would be to me too), they weren't a slight against you. Let him be angry about it. You don't have to pick up that gauntlet.

Doesn't seem overly suspicious if her fears have come true.

Tell her that her instincts were correct without needing to cross the line into invading his privacy and to next time trust herself rather than degrade herself by stooping to his level.

What a jerk though, I hate guys that think they're "playas" so that makes it okay to treat everyone else like a piece of meat for their amusement.

Possibly out of line and more than likely off topic, but what happens when the roommate becomes suspicious of YOU???

I have some sympathy for the roommate, I lived with a lying, manipulative (now ex-) husband and knew in my bones he was back on drugs whilst at the same time thinking I must be going crazy because he protested his innocence so well. But I couldn't understand why we were down at least a grand a month with nothing to show for it.

In the end I went through his pockets and found syringes and dozens of broken methadone amps in one of his old jackets he'd hidden away where he thought I'd never find it.

I didn't feel good for going through his stuff, but ultimately I needed to know my gut feeling was correct.

If I were you I'd be telling her she's better off without him, and arrange a girl's night out somewhere, maybe a crowd of you out on the town.

Possibly out of line and more than likely off topic, but what happens when the roommate becomes suspicious of YOU???

Entirely relevant. Nobody's "gut feelings" are right all the time.

I've known one of my best friends since we were both 10 years old, and there have been instances during our long friendship where I've refused to go beyond offering the basic "yeah that sucks, how are you feeling" type of support. He had other friends to lean on if he wanted to discuss the nitty gritty when there's blood on his hands, since I'm not going allow my friendship be used as an enabling device to encourage my friends to act in ways that I disagree strongly enough with. However, I also believe that blind fealty is a worse sin than being judgmental, so YMMV.

If there's a silver lining for your friend though: that both sides have breached each other's trust now makes it easier to move on, since it makes it obvious that things had really gotten way beyond salvaging. She just needed a smoking gun, and now she has it.

Except that, you've known this person for 15 years. If she's normally irrationally jealous, if this is something that's always bothered you about her, that's one thing. But if she's never been off-base suspicious before, if she's never resorted to snooping in a boyfriend's email account before, and you're mad at her for doing it this time, when her suspicions were entirely justified, then I think that's bordering on crappy.

She is known for being jealous. She's made boyfriends burn letters from and photos of ex-girlfriends before. This is something we've disagreed about for the duration of our friendship. Also, the most recent boyfriend was pushing her to be exclusive, but she wanted to date other people, so I see what she did as slightly hypocritical too. Of course, he was full of it when he said he wanted to be exclusive.

I do feel bad that she's hurting, but am finding it hard to be comforting because of the situation. And that makes me feel like a jerk.

Ahhh. Yeah, for me at least, that totally changes the situation.

"You're better off without him" is both true and supportive. And if there's any way you can non-accusingly bring up the fact that maybe her focus on possessiveness might be attracting the wrong kind of guys, you could maybe go there, but if you're already annoyed, then that may not work well.

In any event, you can certainly listen and offer cooing noises without condoning her behavior. "That sounds hard" or "you sound like you're hurting" are pretty good statement of fact responses that don't commit you to a moral stand, and that can be repeated a great deal more than most people realize in any one conversation before the other person thinks anything is amiss. :-)

Or pretend you're a Freudian psychoanalyst and just say "mmmm hmmm" and "how does that make you feel" for an hour or so, and make her more or less comfort herself.

maybe her focus on possessiveness might be attracting the wrong kind of guys

That's a good point—I'd never thought of that before, but it seems likely. She's pretty open to what I have to say on the matter, but I think I'll save it for when she's had a bit of time/distance from this situation. She knows intellectually that her possessiveness and jealousy do her more harm than good, but emotionally it's a different story. The intellectual-emotional struggle is something I understand all too well.

Oh, and btw, I do think the guy is a playa jerk, and the fact that he misled her is really crappy.

Thanks, all, for your insight and support.