I recently met this guy who seems too good to be true. He's extremely attractive, exactly my type, intelligent, funny and single! We have been on a few dates but have only kissed. Everything seems to be going well, but one thing has been confusing/bothering me. Since one of our first dates, he has been making jokes and comments regarding having a small penis. I asked my friends about it and they figured he was just saying that because it is in fact big, and he wants to make me curious. He made another comment yesterday (probably his fifth) and I just couldn't take it anymore. I questioned him as to why he keeps talking about his small penis and asked if this was a normal joke topic among guys. He told me it wasn't a joke, it was in fact the truth. He said he'd rather I know now, before we have sex (which may happen in the near future) so I'm not surprised.
This attitude is confusing and totally unattractive. I don't know what to think — I've never dealt with a man with a small penis before and definitely not the insecurities that come along with it. I don't know how to react to his jokes, which continued immediately following our "talk." This is odd behavior to me and I'm wondering if this is a normal coping mechanism for guys lacking below the belt. What can I do to make him feel better about himself? — Perplexed Pam
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Dear Perplexed Pam,
To be honest, I'm just as confused as you are! Since you're still in the getting-to-know-you phase, I would think that he'd be doing his best to show you all his good attributes, not wasting time cutting himself down. If he is in fact small, the only reason I'd think he'd continue to talk about it is that he's trying to lower your expectations so you're not disappointed when your relationship progresses to the next level.
I completely understand that his self-deprecating humor is both confusing and unattractive, so I think another little chat is in order. Tell him that talking about his penis size to soften the blow is actually doing the complete opposite. This is obviously an insecurity you cannot relate to, so keep reassuring him of your feelings and the next time he makes a jab at himself, try to stop him before he has a chance to finish. We all know the old saying, "It's not the size of the boat, it's the motion of the ocean," so hopefully his size, whatever it truly is, won't be an issue when you two finally become intimate. Good luck.