Prison School, Hajimete no Gal Recommendations
Both animes have a main character who got a girl in the pilot and will develop their relationship throughout the development of the anime, both have male perverted friends that lack relationship experience, except for one who has theorical experience and shares it with the main character, the humor on both are centered in sexual jokes/events, they share some aspects of both director on some scenes, and made me laugh equally.
Both anime have a group of desperate guys - Nerd with glasses, the main character, a guy who has nothing special and then a fatso with the worst possible fetish. Hajimete no Gal does only have 4 guys though. Even the personality and voice actors of the main character are very similar. And then there are busty females who mess with them.