So, thoughts on women who shave their heads?
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It's a very noble and honorable thing to do, but, I don't think it will get your point across without telling someone that's why you did it. It's not like it's so common that if you see a bald person to think they're supporting cancer, and I'm sure your grandmother would appreciate it, but I'm also sure that your grandmother would want you to be as happy as possible, and it's going to be hard to be happy with your dating life without some resemblance of hair on your head IMO... Plus, you're going to freeze in the winter, and if you're stuck without a hat or umbrella in the rain, well, self-explanatory there. I've never seen a woman (in person) who had a shaved head, and I don't think I'd find myself attracted to her much at all...
Though, that isn't to say that some guy won't come along and fall for you regardless, falling for who you are without any hair at all. And in a way I think it's certainly more respectful that you'd do it because you want to regardless of how others would feel - shows strength of character and independence from others. So - do what you think is best.