Girls are famous for complimenting each other and supporting each other with their words. On the surface, this seems like a good thing. Telling your girl friend that she looks hot before a night out will boost her ego; telling her that the guy who just dumped her wasn't worth her time will help her get over him faster; and telling her that she has a "Beyonce butt" will make her feel more comfortable about her body... right? Wrong.
Also, pointing out problems without solutions is the hallmark of un-helpfulness. So the other important thing to do is to help her find a way to improve whatever it is you are giving her honest feedback about. After you tell her that you actually thing she lost a great guy, for example, don't just stop there and let her believe (wrongly) that she has an inherent lack of ability to get a quality man; tell her that you think you know a couple reasons he might have left, and offer to help her improve in those areas.
When you do these things, you are letting your girlfriend wallow in her mediocrity. If you tell your friend that she looks good when she doesn't, she isn't going to make an effort to look better next time. If you tell your friend that the guy wasn't worth her time, when the truth is that he definitely was worth her time, you are only going to prevent her from doing what she needs to do to make herself more attractive to the next guy of that caliber. And if you tell her that her big ass is sexy, she isn't going to lose the weight she needs to make it look better.
Granted, your girl friend probably isn't naive enough or dishonest enough with herself to completely believe you when you say these things; but I am willing to bet that neither is she wise enough nor honest enough with herself to disbelieve them completely. By telling her anything less than the complete truth, you are placing a Band-Aid over the wound; you aren't substantially helping her. Or worse, you are cowering from your fear of telling her the harsh truth, only because you want to avoid the confrontation that it might cause. Even your excuse about making her feel good about herself falls flat, because a girl's "need to feel beautiful" cannot be satisfied by empty or equivocated compliments.
The problem with this kind of "support" is deeper than just the effect that you have on your friend. Not only are you wrong about the fact that you are helping her, you are probably also wrong in believing that your motive was to help her in the first place. You tell her that she looks hot because you think she needs to hear that she looks hot. But that is just a symptom of the fact that, if you were in her situation, you would feel the need to hear that you look hot - precisely because you wouldn't believe it. And you tell her that her ex wasn't worth her time mainly because, if you were in her situation, you wouldn't be comfortable with accepting the harsh reality that he was absolutely worth your time, but you lost him. And if you had an ass that size, you'd want to believe that the shape compensated for the size, because you'd hate having to face the reality that your ass is huge, and that you actually need to start a real workout, rather than just reading magazines on the treadmill three times a week. In other words, your inability to be honest with your friend is a reflection of your discomfort being honest with yourself.
Granted, there are right ways and wrong ways to break the news to your friend that she is fat, or looks bad, or just lost the man of her dreams - or any other news she isn't going to want to hear. I am not suggesting that when she asks "doesn't my ass look big in this?" you reply "yeah, like huge!" There are ways to get the truth across tactfully, one of which is not embarrassing her in front of others. For example, in that situation (assuming there were others present), you could say something like "It's probably not the right dress for you" and then later - in person - tell her that she should throw it away.
Also, pointing out problems without solutions is the hallmark of un-helpfulness. So the other important thing to do is to help her find a way to improve whatever it is you are giving her honest feedback about. After you tell her that you actually thing she lost a great guy, for example, don't just stop there and let her believe (wrongly) that she has an inherent lack of ability to get a quality man; tell her that you think you know a couple reasons he might have left, and offer to help her improve in those areas.
By starting to be more honest with your girl friends, you aren't going to start a revolution in the way that women give each other feedback and advice. This is something rooted in female nature, in the same way that the male inability to engage each other emotionally is rooted in theirs (and neither is a strength). But you could do something far more important, in the sense that it affects you a lot more: you could change the culture in your group of friends. If one or two of you start breaking the insincere compliment cycle, the others will catch on, and soon realize that yours is a better course of action. The more you foster that culture among your group of friends, the more you all will benefit from the mutual honesty, the more you will improve yourselves and your chances with the opposite sex.
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