Philip Van Munching from Darien, Conn., is a finalist in the Dear GMA Advice Guru Contest. Read his 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."
Philip's Answer:
How do you tell someone she's a laughingstock and NOT hurt her feelings? Sherema, if you figure that one out, I'd encourage you to immediately start on a cure for cancer and a solution to the Kennedy assassination, because you'd be a miracle worker. (Sorry; couldn't resist.)
Actually, I think there are two approaches to this, the first being the dropping-hints-the-size-of-minivans approach. For instance, you might invite her over and switch on any TV show that has a title starting with "The Real Housewives of…" While watching, you can point out how ridiculous at least half of the regulars make themselves look by trying to offset their Botox with Juicy Couture. Of course, the problem with this approach is that she might laugh right along with you … and never realize that she looks just as silly when she's at the office.
Better to go (mostly!) directly at the issue. Do it someplace away from the office, when you're having a relaxed conversation. And don't – repeat: don't – set up the subject with any version of, "If you thought I was doing something wrong, I'd want you to tell me," or, "I want to tell you something, but I don't want you to be mad." Either of those would likely get her so revved up going in that she wouldn't be able to hear what you have to say.
Instead, find another way into the subject. Maybe something like this: "You know, I was looking at the website for this great charity I read about; it's called 'Dress for Success,' and what they do is help disadvantaged women get – and keep – jobs. One of the ways they do that is by providing business suits and other clothes that help them look as professional as they can. I guess the thinking behind it is that, in a working world that can be very judgmental toward women, we have to do everything we can to be taken seriously. That made me think of you, because I notice that you dress very young and very casually, and I wonder if you're doing yourself a disservice without realizing it."
Now is the time, Sherema, when you can put a little disclaimer on what you're telling her: "I hope I'm not out of line by saying that." If she says you are, back off. You've planted the seed, and often, that's the best you can do. But notice how you did it without mentioning the word "laughingstock," or making her feel like others are judging her?
If she lets you go on, you might tell her just how attractive you think she is…and that you think she'd still be a real knockout in business clothes and more subtle makeup. Either way, have the conversation once, and let it go. Believe me, she'll start to be more aware of how others are perceiving her at the office.