Beauty Blunder 5: How-to Tell A Friend Their Look Is Bad

Question: My 50 year old brother-in-law visited recently for a family birthday party. I strongly suspect he is cutting his own hair. Most of the cut was unremarkable but a portion (think of the state of Florida) was too long on the back side of the head. I am sure about the Florida part.

I did take pictures but, in kindness I avoided that offensive spot. If it was a small state like Delaware or Rhode Island then 'NO PROBLEM but this was FLORIDA!  How do I let him know he should turn on the lights when he cuts his hair? I don't want him to be embarrassed. How do I fix this blunder once and for all? -Joe

Answer: That was so entertaining to read!  It sounds like you have a great sense of humor which will be crucial in your bringing up this beauty blunder.  

I think it's best to be straightforward when someone has a fixable flaw.  It's like the moment when a person smiles at dinner & they have a string of something hanging from their teeth.  Or when there's a trail of toilet paper attached to a stranger's foot.  Do you say anything?  I do.  If you don't make it into a big deal, your brother-in-law probably won't either.  

You could bring it up without mentioning that you think he cuts his own hair.  You might want to say something like, "Hey ___, I think your stylist missed a spot in the back," or you can try to be funny. "Have you been letting my sister near the scissors lately?"  This will let him know you're looking out for him, & he'll trust your honesty.  If you aren't comfortable approaching your brother-in-law, you can always mention it to your sister, or your wife (whomever is closest to him.)  He'll probably be happy to know about the spot, so he can fix it & feel secure.  

Good luck!