Dear roommate: You are beautiful. Please realize this.

My roommate is awesome. Especially considering I went through the lottery and could have ended up with anyone, she's great. We talk about stuff, we're friends, she's funny, she puts up with my obsession with Supernatural--basically she's great. I'm really sad she's going abroad next year and I have to go through the lottery again.

But here's the thing. She's beautiful. If I were going to switch appearances with someone (which I wouldn't, not having self-image issues), I would pick her. But she has serious self-image issues. I tell her she looks great, I point out that there's actually nothing wrong with the things she's picking at; but she just thinks I'm being nice so I won't hurt her feelings. What am I supposed to do? She brings it up, so I can't just not talk about it. Considering the amount of time she spends hiding these perceived flaws, I'm pretty sure she thinks they're real, so I can't ignore her when she does bring it up. It's doubly bad because she reminds me (appearance- and voice-wise) of my ex-girlfriend, who had even worse self-image issues and took some drastic measures to deal with them; so this worries me.

Help?

Difficult, as girls with poor self image are about the hardest people to convince of the truth, but... All I can suggest is a campaign of compliments when she's not actually thinking about her own appearance. I have no idea what your room-mate looks like, but something comparisons like "You look a bit like Salma Hayek in that top," or just mentioning that she looks really good, or that her hair looks nice today, or a colour suits her - off hand compliments, whenever you notice how nice she's looking. Make them specific rather than vague "You're really pretty type things, which are very easy to dismiss.

And when she's putting herself down, just contradict her. She won't listen to you then, but she might gradually, and subconsciously, pick up the message from the compliments she receives - and probably dismisses - when she's not even thinking about how she looks.

You have a female roommate? O.o
But yeah, I kind of agree with alysdragon. When she doesn't have any makeup or anything on tell her that is beautiful. Try to convince her that she doesn't need five pounds of makeup to make her look goreous.

Maybe you could try challenging her: Tell her to go one week (or however long) without makeup, and see how many compliments she gets. Don't forget to compliment her as well.

I'd be interested in how to handle this too. I have a roommate who has self-image issues (constantly commenting on how "fat" she is at 115 pounds, or how "ugly" she is when she actually looks good - and that's without makeup most days) and I handled it in entirely the wrong way. I started off doing what it sounds like you're doing - just contradicting her every time she brought it up and complimenting her at other times, but it got really frustrating because, of course, she never listened. Eventually (after about a year and a half), she brought it up on a day when I was already in a bad mood and I snapped and basically told her to shut up about it because it was really annoying. This was several months ago and she hasn't mentioned it to me since, but I feel bad about it because I know that was definitely not the right way to address the problem.
I'm left wondering if a good way to deal with it even exists, since telling her she's wrong doesn't work.

I wonder if there are people/things that constantly trigger her self consciousness? I know with me, I would, and still, get kinda moody whenever people bring up that I look good (though some old fat lady kept on talking about how ugly she thought I was). The reason I hate it when people talk about my appearance is that's all they seem to focus on. Once my therapy sessions were sabotaged just so I could go to a doctor to lose weight, despite the fact that I told them that I stress eat. It was like I could have just put up a picture and no one would have noticed that I left for the week.

It took a lot of encouragement from my guy that I was valuable as myself, and ultimately moving out, that got me to accept that I am a pretty woman. The tomboy in me hates to dwell on that, but I finally got past being overweight, not having "good hair" and not caring too much about the latest fashion trends.

It sounds like she's hurting in a way that goes beyond appearance. What she might really mean is that she doesn't think she's good enough in some other area of her life and the only way to communicate this to anybody is to talk about appearances only. I went through the same thing. During a low point in my life, all I would focus on is the fact that I was ugly. It turns out that being ugly wasn't the problem--I just didn't know how to cope. So instead of getting help, I'd talk about it, lose all of my friends and ultimately deepen the idea that nobody wanted to be around me because of how I looked. (Which really wasn't the case--I'm just not a fun person to be around in general).

When dealing with this, I would suggest not talking about appearance at all. If she brings it up, don't feed into it by showering her with compliments (because it hasn't been working, so why continue doing it?) Instead, ask her how she's feeling, how her day went, etc. Talk about who she is as a person and try to get around the popular notion that people are to be valued based on how they look. If this doesn't work, a therapist might help, but I'm not sure how receptive she'd be to that idea.

Of course, given the information that you've provided, I don't know the full story.
In any case, I wish you luck.

How she sees herself isn't going to change because you compliment her it sounds like, that self confidence has to come from within. So I would agree, don't give all the compliments when she thinks you're only being nice because you're her friend. Plus in my opinion when someone who compliments people less the compliments they do give mean much more and have a bigger impact.

I'd say, don't talk about your apperance. Don't talk about hers. If she mentions it, polietly tell her that she's wrong, she's pretty/whatever, and leave it at that. From someone who can be incredibly self-concious, when people bring up my apperance, it reminds me that I have one. And I don't like it. So I get really awkward and shy. Them talking about themselves, does the same thing. >.<

My advice would be to build up her confidence on other things. Does she know multiple foreign languages, complement her on that, if it comes up. Does she get really good grades, really good at something else? Complement her on that. Don't fake any complement, and don't overshower her with them in unneeded situations. I feel more self-concious about myself whenI forget I have an apperance. For me (and maybe I'm wrong, I don't know your roommate and can only speak from my perspective on this) talking about at all brings in insecurity. And unease. *shrugs* It's way easier to be objective from an outside point of view on things like looks. >.<