Dear 'GMA' Advice Guru: Kimberly Giles

December 8, 2010 -- Kimberly Giles from Bountiful, Utah, 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."

Kimberly's Answer: This is a great question, and having a conversation with your friend would definitely be the loving thing to do. The good news is, it's not hard to have these sensitive conversations in a loving way. You can do it!

Here are a few suggestions…

1) Find the right time - You want to have this conversation when you are alone and won't be interrupted.

2) Ask permission to discuss a sensitive issue - "Would you be open to talking about something kind of personal with me?" (Wait for a Yes)

3) Ask whether she feels safe with you - "Do you know I care about you and only want the best for you?" (Wait for a Yes)

4) Ask her what she thinks and feels about the key issues - "How important do you think it is that our co-workers take you seriously and respect you?" (Listen) "How much do you think the way you look might play into this?" (Listen to how she feels about it)

5) Ask permission to speak your truth - "Would you be open to some constructive criticism from me, even if it hurts a little to hear?" or "Would you be open to some brutal honesty, knowing that I love you?" (Wait for a Yes)

6) Speak your truth - "I believe that the way you dress and the amount of make-up you wear at work, effects the way people respond to you. So my question is… Would you ever be open to some suggestions about how you might dress and do your make-up differently to create a more professional presence? Would you ever be open to letting me help you with this?"