I really didn't think John was hideous looking or a loser. He's a normal looking dude with a decent job and a really sweet personality who has been depressed for a long time. But the fact that he was completely honest from the get-go would probably have been really attractive to a woman like Molly.
There were actually quite a few moments in the film that really highlighted how sweet and open John could be. I mean, when he gets so excited at the prospect of Molly visiting his house after work the day after the party and cleans everything, and prepares a nice dinner, and tries to look presentable, how could you not be like, "awww, that's pretty adorable". There is definitely something appealing in being with a person who always seems to be so thrilled spending any moment with you. Besides, it's pretty clear she needs a sensitive guy who could understand the relationship with her son. Actually, I think he probably reminds her of her son a little as well.
I don't know if you're joking about the penis thing, but that's pretty stupid. Clearly she was just making a joke and was interested in talking to him because of hearing him open up at the party.
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