How to Tell Someone Something Embarrassing

My wonderful, beautiful wife often has residue from salad between two of her front teeth. Or we'll arrive somewhere and her lipstick has somehow transferred from her lips to her top front teeth. Should I or should I not tell her? I love her the way she is and don't want to make her feel insecure by pointing out such minor flaws. N.A., Philadelphia

You have to make a joke out of the fact that everything that lands on her front teeth seems to stay there. Tell her you don’t want to embarrass her, but ask if she wants you to tell her. Chances are she will welcome a subtle hint. Have an expression you use in conversation, such as “the horse is out of the barn on that one,” to suggest something is awry. You can use body language to signal her by taking your straightened index finger and running it horizontally along your upper lip to let her know there is something askew under that painted lip.