My friend was dating a guy and after they had been intimate a few times, he asked her if he had the biggest penis of anyone she had been with. First of all, that is a totally weird question (guys are always obsessed with size). Secondly, don’t ask the question unless you are prepared for the answer. She answered honestly and said “no.” He was a decent size, but the truth is, she had been with a guy who had a bigger penis. He demanded to know who and she told him. Not like it mattered, since he had never met the guy before. After that, it was an ongoing point of tension. He constantly mentioned this other guy’s name and was always asking about why she wasn’t with him if his penis was so big. Penis size isn’t everything and being wildly insecure about yours, and always talking about your insecurities is a complete turn off.