Dating while bald

Have a safe and happy 4th. No chat today. Here's a holiday letter.

Hi Meredith,

I know this is a bit of an atypical question. I'm a 30-something who has been able to snag some very beautiful and amazing women in the past. I've always been confident in that respect, but the last few years my hair has been thinning on top, and my confidence isn't what it used to be.

Now I've heard lots of people say that there are plenty of attractive balding men and that balding shouldn't hold you back at all. But at the same time, I've never heard a single woman say how attractive they find thinning hair or balding men to be. In fact, when I wear a baseball cap, I get a ton of female attention and most women check me out. When I'm not wearing it, I get far less, so I know firsthand that it makes a difference. It's gotten to the point that when I'm flirting with a girl with my hat on, I get self-conscious about what she'll think when I take it off.

I know, given the choice, a woman would rather have great hair on her guy than the thinning variety. My question is: Is my thinning hairline drawing as much attention as I think it is? What would make a beautiful woman, who has options, look past this unattractive quality? If I ask a girl out who met me with a hat on, should I expect her to be disappointed when she sees me sans cap? I'd really love to know from a woman's perspective, as I've been too shy to ask, yet these questions run through my head anytime I'm talking to a beautiful girl I otherwise click with.

Sorry ... but I guess boys can be vain too. Thanks.

– Anxious About Follicle Challenges

Bald doesn't bother me. Bald can be great. It's all about confidence and wearing it right, AAFC.

Wearing it right is so important. You mention that your hair is thinning on top. Please ask a hair stylist or stylish friend whether you should keep the hair you have or just shave everything off. That can make a big difference.

I know it sounds cheesy, but the rest of this is about self-confidence. You must remember who you are and what you have to offer. You must forget about your hair when you're talking to people. You have to keep that cap off as much as you can. Don't walk around looking like you have something to hide.
You don't have to be a guy who's going bald. You can choose to be a cool guy who just doesn't have much hair.

Figure out how to wear it -- and then work it.

Readers? Advice? Is it all about confidence or do women want a guy with hair? Is thinning hair worse than just being bald? Are you sad when someone takes a hat off and you find out that there's no hair under it? Help.

– Meredith