Although your friend may broach the topic in a nonchalant way, there is often a lot of emotional worry that comes with it. Just because she mentions it breezily doesn't mean you should wave it off or reply without considering your answer. If the question comes your way, do your due diligence. Think about your friend, what you know about her and where the question stems from. It's a sensitive issue for many, so tread lightly.
Remember that how a woman views herself is all about her own perception. A woman who is 105 pounds can look to the centimetre of fat on her belly and feel unsatisfied, while a woman who weighs far more may be completely fine with a little bit of belly fat. Self-perception is in the mind, and though we can help a to friend see herself in a more positive light, it isn't fair to judge or belittle any negative feelings she may verbalize, because we cannot know what is going on in her head. So instead of trivializing your friend's concerns, allow her to speak her mind fully. Sometimes just putting into words how she is feeling about herself may be all she needs.
Women can ask this complex question in a variety of situations for many reasons. It is important to take these unique scenarios and motivations into account before replying. If the question is posed once you are already at the specified event, telling your friend she doesn't look her best won't accomplish a lot. She's already left home, so she can't change what she's wearing and remedy the situation. All she will do is spend the remainder of the evening unproductively stewing over her appearance. If, however, she asks you while still at home before the event has begun and has other wardrobe options to consider, there is room for a little more honesty.
It is the duty of our clothes to make us look as wonderful as possible. An ill-fitting dress really can make someone look larger than they are in reality. If a dress is too small, cuts in at the wrong place or isn't tailored to a person's body correctly, it can be unflattering. Although your friend may be fixated on how she feels she appears in the mirror, how she looks may have far more to do with what she has on than her actual size. As a good friend, of course you want to be honest and send your pal out into the world looking her best. Sometimes focusing on the flaws of the garment rather than the flaws she may be seeing in herself can get her to change looks without getting down on herself.
Ultimately you want your friend to look her best. But looking one's best has a lot to do with feeling good about oneself. Taking a question of this nature too lightly or being overly harsh with your answer can have long-term negative effects, so it is important that you assess the situation and do your best to be honest while still being sensitive to how your friend is feeling.
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