Looking for recommendations - similar tone as The Graduate

Hi there, haven't posted here in ages. I've been looking for some movies similar to The Graduate and The Heartbreak Kid. The unconfident (or perhaps over-confident depending how you look at it) male who's chasing after a gal. They're not overt comedy films, but I like when the male character is just exaggerated enough to be both funny and also recognizable. Just watched Gregory's Girl which hits some of the same notes. Sorry that it's pretty specific haha, just wondered if anyone had any suggestions.

Rushmore (1998)
Tadpole (2002)
Adventureland (2009)
The Way Way Back (2013)
The Flamingo Kid (1984)
Class (1983)
Heaven Help Us (1985)
The Sure Thing (1985)
Say Anything... (1989)
The Rachel Papers (1989)
Sing Street (2016)

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"Film is a disease. When it infects your bloodstream it takes over as the number one hormone. It bosses the enzymes, directs the pineal gland, plays Iago to your psyche. As with heroin, the antidote to Film is more Film." - Frank Capra

A lot I haven't seen, thanks!

Maybe Goodbye, Columbus?

chilly scenes of winter

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letterboxd
criticker

Good movie and that's the first time I've ever heard that mentioned here.