Not exactly a book, but a short story, young-adult maybe. From what I can remember, the story was relatively short, something around 20-30 pages, maybe ? I remember reading the story about 8 years ago or so but the story could've been much older. I remember it being a Roald Dahl piece (short story compilation-ish) but I could be mistaken on that one. A good portion of it was the first person perspective of a middle/high school boy that has a tall, awkward girl as a normal friend but somehow manages to catch the eye of a really popular and pretty girl and goes over to the pretty girl's house to ask her about prom.
He can't believe his luck but it turns out the popular, pretty girl is rude, entitled, spoilt and is a very attention-seeking, compliment-fishing person. Before prom, he meets her dad who's a muscled brute who shakes his hand squeezing hard to show some sort of dominance but the meeting goes haywire from there with him running away from the house and the pretty girl's father chasing him in the darkness while mentioning something about serving in Vietnam (very quick escalation, I know, lol).
He then asks out the tall, awkward girl to prom and in turn goes over to her house to meet her dad. The dad is a gentle giant, is kind, soft-spoken and shakes his hand very gently. The awkward girl turns out to absolutely beautiful in her prom dress and he realises he's had deep feelings for her all this time.