Why is it the ugliest men are the boldest? I had a random impromptu marriage proposal from a guy with few and/or broken teeth a while back (not the first from an ugly man). Then I went on a horrific date last night with an ugly dude whose mom hooked us up (I was there for free food) and this man asked "how are we going to work the bill?". And why is it the ugliest dude in the club will stalk you the entire night? Can someone please explain this ugly man boldness phonomenon cuz I'm not getting it? If I was ugly I'd go hide myself somewhere.