December 8, 2010 -- Liz Pryor from Studio City, Calif., is a finalist in the Dear GMA Advice Guru Contest. Read her response to a viewer-submitted question below!
Question from Sherema in Orange Park, Fla.:"How do I tell my best girlfriend that the ton of makeup and skin tight clothes designed for teenage girls makes her a laughing stock at the office and not hurt her feelings? She is a very attractive 49 year old lady but her appearance makes it hard for our co-workers to take her seriously."
Bottom line? There is no possible way to tell your best friend that her co-workers laugh at her because of the make-up she wears and the tight-fitting clothes she sports. There isn't a woman on the planet who wouldn't be hurt by this, no matter how you spin it. Since you're her closest friend, you must know the kind of time and effort she puts into looking like such a hottie. Unless you forgot to mention she's blind, she is well aware of what she puts on every day. This isn't one of those cases where you say, "You may not realize it but…" because clearly she realizes, and takes pride in exactly what she's wearing on her face and her body.
I'm sure, like most best friends, her clothing has come up in the past, no? She is most likely aware you would not choose to borrow most of her wardrobe, and that's fine, to each her own. If you do choose to tell her and include the co-worker's thoughts on it, to sort of back your case, it could open a huge can of hard-core office drama that could easily put this great friendship and your work environment at risk.
However, something to think about - if your friend were to come to you and ask you why the co-workers don't take her seriously, it would turn this around and allow you to offer the information in a way that would feel constructive for both of you. I imagine there's a lot of history, a lot of laughs, a lot of phone-time, a lot of good life shared with this friend. You might think about all of that, before making the decision to confront this. If the look is so distasteful, the boss will tell her to tone it down; that's his job. I suggest you measure the risk here very carefully. Sometimes it can be of great service to our lives to curb our unsolicited advice.