Recommendation: Uchiha Sasuke versus the United Shinobi Nations
https://archiveofourown.org/works/59616685/chapters/152052802
Pairing: Uchiha Sasuke/Uzumaki Naruto
Summary: Konoha after the Fourth Shinobi War, he doesn't have a lot going for him: no permanent address, dubious career prospects, a small fortune in overdue fines at the public library, and—worst of all—some kind of complicated feelings situation going on with his best friend, whose bed he happens to be sleeping in.
But asking Naruto out turns out to be the easy part, even if it happens mostly by accident. No, the real problems arise after that, when Sasuke finds himself challenged to single combat (or strategy board game) by every single person Naruto has ever had a thing with. Even without much (any) firsthand romantic experience himself, Sasuke is pretty sure that isn't normal. But hey, in between dodging village council meetings and avoiding folding his laundry, at least it gives him something to do.
Basically: The plot of Scott Pilgrim versus the World adapted to Naruto.
This is peak fanfiction. Art. The single most hilarious thing I've read in the fandom. I haven't stopped laughing since I opened it.
Imo, the hardest form of writing to pull off is balancing humor while still maintaining emotional beats. suspiciousflashlight manages it flawlessly.
Strongly recommended. I'm not a romance reader, I'm not at all a NaruSasu shipper, and I still loved it.