If there was ever a list for the most unlikely of heroes in all of anime, One Piece's Usopp would be among them. This long-nosed sniper is the Straw Hat Pirates' resident sharpshooter, as well as a bit of a coward and a liar who tends to find himself in some dangerous situations - but he's no slouch in a fight by any means.
Over the years, Usopp has come into his own as a pirate and has gone on tons of adventures with the Straw Hats, but not much in the pursuit of love. While romance really isn't the focus of One Piece, it is interesting to speculate the kinds of anime personalities out there that would get along with the Sniper King himself, despite some of his faults.
10 Sheska: A Total Bookworm Who'd Like Hearing His Stories (Fullmetal Alchemist)
If there's one thing to say about Fullmetal Alchemist's Sheska, it's that she has an undying love for reading. A bookworm to a fault, Sheska often throws herself into the pages of a book, sometimes to her detriment. She's also got quite a bit of low self-esteem, much like Usopp.
On top of being birds of a feather in their low self-confidence, Usopp's stories (about his real adventures and the ones he's made up) might just be something Sheska would like to listen to - perhaps even writing a book about them.
9 Charmy Pappitson: A Food-Crazed Personality That's Easy To Get Along With (Black Clover)
By this point, Usopp is used to seeing Luffy fill his black hole of a stomach, so those with big appetites probably aren't too much of a shock to him anymore. He's had something of an appetite himself, especially when he was stranded on the food-filled Boin Archipelago, so someone like Black Clover's Charmy would be easy for him to get along with.
Similar to Luffy, Charmy is generally carefree and always looking for a good meal - though, unlike the Straw Hat captain, she does enjoy sharing food with others. Despite her small stature, being part dwarf, Charmy is also one tough fighter with her cotton magic, perfect for Usopp to hide behind in hairy situations.
8 Aqua: Useless Maybe, But Probably Willing To Believe Usopp's Tall Tales (KonoSuba)
While Aqua would try to have people believe that she's a powerful and competent goddess in KonoSuba, she's anything but. Much like Usopp, she's a cowardly liar who talks a big game that lands her in hot water most of the time.
On top of having similar personalities, Aqua is also incredibly gullible and believes that nobody is capable of lying to her, which could work out in Usopp's favor, since Aqua would believe all of his stories no matter how out-there or made up they might be. Not to mention, Aqua's ability to ward off ghosts would interest Usopp.
7 Kale: The Two Are Timid, But Fierce And Loyal (Dragon Ball Super)
While Usopp can be a big coward in the face of danger, he's still loyal to his friends and tries to help however he can despite his fears. Over time, he did actually become fierce in battle. With all that in mind, he has some similarities with the timid Saiyan warrior from Dragon Ball, Kale.
Kale is rather meek and often feeling negative, but she'll jump into a fight if her friend Caulifla needs help. In a way, she and Usopp are kindred spirits, though Usopp should be careful whenever Kale rages out into her Legendary Super Saiyan form.
6 Kumoko: Good Thing Usopp Likes Spiders (So I'm A Spider, So What?)
Usopp is known for being afraid of a lot of things, yet surprisingly one thing he's not is an arachnophobe. Apparently, Usopp used to play around with spiders when he was a kid, so he's developed a certain fondness for the eight-legged creatures. This might be something that Kumoko from So I'm A Spider, So What? might take interest in him for.
While her monster spider form may interest Usopp, Kumoko's Arachne form could better communicate with him. On top of that, Kumoko's plucky and invincible optimism might be a good influence on Usopp, who could definitely do with a positive attitude.
5 Ristarte: The Two Are On A Similar Wavelength (Cautious Hero)
Cautious Hero's goddess of healing, Ristarte (aka Rista) is already used to dealing with the most cautious of individuals, so someone like Usopp would be a walk in the park by comparison. Her immense abilities in healing would also jive well with Usopp's perseverance and dumb luck when it comes to trying to stay alive.
Aside from that, Rista and Usopp do seem to be on something of a similar wavelength, freaking out in over-the-top fashion during tense situations, while still sticking by those they care about no matter what. Unfortunately for Usopp, Rista may only have eyes for Seiya.
4 Rosetta: A Shared Appreciation For Plants (Granblue Fantasy The Animation)
After his time on the Boin Archipelago, Usopp has developed something of a green thumb thanks to using the Pop Green seedlings as his ammunition. Even before that, one could say Usopp had a level of appreciation for nature - enough to catch the attention of a certain Primal Beast of the forest.
Rosetta's intentions in Granblue Fantasy are often a mystery to many, but she's very kind to those around her, and she loves gardening, which compliments her plant-based powers. Given hers and Usopp's shared interests in plants, they might just make an unexpected match.
3 Mey-Rin: Snipers Gotta Stick Together (Black Butler)
Usopp is not the only famous sniper in anime history - there are plenty of sharpshooters out there that could give him a run for his money. One example is Mey-Rin, a maid of the Phantomhive house in Black Butler who may seem awkward and clumsy, but like Usopp, there's more to her than meets the eye.
Mey-Rin is actually a very talented sniper whose far-sightedness makes her able to pick off enemies with extreme accuracy without even needing a scope. Having similar talents, the two would make a pretty unstoppable team.
2 Sabrina: She Appreciates A Guy Who Makes Her Laugh (Pokémon)
At first glance, the Kanto Region's Psychic-Type Pokémon Gym Leader, Sabrina, seems like a cold and distant individual whose emotions are locked up tight. This is actually true, but after encountering a very goofy Haunter, her love for humor and being able to laugh became more apparent.
Given all the hilariously out-there expressions and reactions that Usopp has pulled off, as well as all the funny stories he told Kaya back in the day, Usopp would be one of those people who could make Sabrina laugh. She might just be able to appreciate the pirate based on that alone.
1 Yoko Littner: A Sharpshooter And A Mecha Pilot (Tengen Toppa Gurren Lagann)
Gurren Lagann's Yoko is a sharpshooter who's able to take out tough foes on her own with nothing more than her sniper rifle - even the sturdy and strong mecha Gunmen. On top of that, she's a skilled pilot in a Gunman of her own, able to fight with the best of them.
With her marksman abilities and Usopp's fondness for robots (if his reactions to Franky and all his gadgets are any indication) then there's a great chance the two would get along rather well. A nice, yet unlikely pairing.