Dear Dr. Shubs,
I’m a 40-year-old man, and my hairline has been gradually receding. Last week I finally decided to get a toupee. I like the way it looks, but I’m still not comfortable with wearing it or how to deal with it in dating. What should I do when I go out on a first date? Do I tell her about it before I go? How long should I wait to tell her?
“Top Up or Down”
That’s a hairy question you’ve raised! The real issue here is one of honesty and intimacy.
Some women don’t like bald men, others do, and still others don’t care. Obviously you’re not comfortable with your baldness, which is why you decided to go for the toupee. If you think of the baldness as standing for whatever you feel insecure about, that insecurity is exactly what the toupee is covering, not just your head.
So, you may find your answer by asking yourself some questions. When would you like to find out that a woman you will be dating wears falsies, or may wear a wig of her own, or has had a mastectomy? Imagine how you would feel if and when you were told about those things.
Look to see what you might be afraid of if you wouldn’t want to date such a woman. Whatever your answer is, that’s probably what you’re afraid she’ll be thinking about you, too.
In any case, be sure to tell her some time before she finds out for herself. She may already have figured it out by then, but the fact that you are telling her will go a long way to opening up the intimacy between you. And, you certainly don’t want to her to discover it for the first time when you are in the throes of passion and she is running her fingers through your hair and thinks she has scalped you.
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