Appearances aside, they were extremely compatible and worked well as a couple. Same wit, humour, personalities and interests. If they also had a fulfilling sex life I can't see why they wouldn't be together.
Maybe Lisa's hotness prevented other more conventionally attractive guys from hitting on her and she liked the fact that Vinny had the balls to go after her and she found him really funny. He was also not afraid of a fight and obviously quite capable of handling himself despite his average height.
He took out TJ with one single punch (albeit a bit of a sucker punch lol). Maybe when they were out on their first date some guy made a comment about him or Lisa and Vinny put him in his place with a wise-crack remark and then when challenged he beat the sh!t out of the guy just for good measure.
Lisa and Vinny both come from a background were honouring your man and lady and important, so his charm and protectiveness of her would most likely score very highly with her and her family. Vinny was working at her father's garage at some point during law school, so perhaps they met there or even grew up together.
I know in real life they 're 21 years apart, but I got the feeling that in the film Lisa was meant to be later 20s and Vinny mid 30s, so a round a 7 to 8 year difference, not something that would really be frowned upon if they started dating when she was 18-19 and he was 26-27 and he was a nice respectable Italian guy from the neighbourhood.
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