 If you liked
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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 ...then you might like
Make Heroine ga Oosugiru!
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This shows are wry, conversational high school romantic comedies that sarcastically comment on and deconstruct the differences between high school rom-coms and (notional) real life. Also, in both anime, the protagonist is a snarky and prickly, but sympathetic and kind person inside, who sincerely helps girls cope with their psychological problems. By the way, the author of Losing Heroines calls Oregairu one of his favorite LNs, so the similarities are most likely not accidental.
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Recommended by RobertBobert
Also about a guy who doesn't normally interact with girls being put in a situation where they develop some kind of friendship and get closer over time. Both are quite slow moving in the romance sense and are a lot about the male character development.
The interactions between the characters has left me the same vibes in both shows, despite being more complex in Oregairu
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Recommended by julanthoann