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Oh please, Dino, that's like saying I, pretending that I'm single, should go out and get my breasts enlarged because a guy may decide mine are too small.
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That's different.
1. boobs are on show at all times, rather like a massive erection.
2. boobs don't provide any physical sexual pleasure, only fetishistic excitement.
Men who like women with large breasts generally don't flirt with women who have small breasts - like I said, they are on show at all times, so it's pretty easy to tell when a woman has large breasts as opposed to small ones. (padding and implants excepted)
And we're talking about Matt's confidence and self esteem here, which is helped by avoiding situations where a woman can make nasty comments about him when they find out that he has a small penis. He probably doesn't want to have to explain to everyone that he has a small dick, least of all a hot date who he's trying to impress.
I appreciate what you're saying, penis size isn't everything - but the fact of the matter is that not a lot of people realise this, and that can't be helped or changed.