Should I bleach my hair blonde?

I lost a bet made about the NCAA tournament, and I'm supposed to bleach my hair blonde now. The guy I made the bet with says I don't really have to do it, but I kind of want a change. I'm wondering if any hair experts out there woul be able to tell if I would look okay or not with blonde hair, you can look at my photos to see. I have reddish/brown hair, kind of fair skin, a reddish beard. Thanks in advance.