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If you liked Wotaku ni Koi wa Muzukashii add

...then you might like Horimiya add

Both of them have a shy love interest and a outgoing MC girl. Both have side couples with a diffrent interesting dynamics. Both are pretty laid-back and dont have that much drama or action. Comedy. MC teaches shy dude to love. Both couples get togheter fairly early.

If you liked SK∞ add

...then you might like Bakuten!! add

Both have a main character that is scared of being surpassed by others (or not catching up to them). Both have a shy side character thats unexpectedly really good. Side characters: andry simpleton (s), pretty glasses dude thats calm and little punk. Sports, very competition oriented. Has a one-off episode where they just chill. REALLY GOOD OP/ED.

If you liked Free! add

...then you might like Re-Main add

Both have swimming. MC quit a sport and starts playing it again in highschool. One character (or more possibly) learn the sport from scratch. Good OP and ED. Hot dudes getting wet (IN WATER).