Made this "little" list to organize all the Usopp ships I have (from the most-likely canon to the rarest rarepair, also according to their age difference). I did this because I wanted to put into words how Usopp interacts depending on the relationship (spoiler: he's a chameleon)
You can add additional thoughts in the comments 🤭
Usopp: Considerated, liar
Things in common: Like stories, have childhood memories, love nature, great with kids.
Tropes: Shy x shy. Funny guy x smart girl.
Other headcanons: Acespec couple
Development: Pre-time skip
Love language: Quality time, receiving gifts
Negative: Misunderstandings, sometimes Usopp needs to be more serious and on the other hand lack of words of affirmation in Kaya's part.
Usopp: cautious, prideful
Things in common: Love for bugs, like stories, adventure, games. Generally in sync with topics.
Tropes: Friends to lovers / queerplatonic / found family. Other Headcanons: Aroace Luffy, Pansexual Usopp.
Development: Pre-time skip
Love language: Physical touch, quality time
Negative: Miscommunication/No communication can turn into conflict (captain vs subordinate)
Nami: Caring, fierce, stubborn
Usopp: easy-going, indulgent
Things in common: Love gossips, teasing, find comfort in sleepovers and conversations
Tropes: Besties to lovers. First kiss.
Other headcanons: cuddles. Queerplatonic
Development: Pre-time skip towards Post-time skip.
Love language: receiving gifts, quality time and physical touch.
Negative: stubborness by both parts (not wanting to ruin their friendship) can lead to angst.
Sanji: servicial, overwhelming (both good and bad)
Usopp: talkative, insecure
Things in common: Passionate about their dreams. Care for each other. A little bit of similarities about their parents (ill moms).
Tropes: Friends to lovers. First relationship. Usopp fell first but Sanji fell harder.
Other headcanons: can get in sync pretty easily (ending the other sentence, teasing Zoro (example: Sabaody). Pan Usopp and Genderfluid bi Sanji. Usopp gives him flowers and edible seeds/spices and Sanji makes his favorite dish at least once a week. Personal taste-tester. Kitchen (and midnight) conversations. Stargazing. Matching lightning scars. Sanji likes to trace Usopp strech marks and called them beautiful. Sanji loves Usopp body (not inherently sexual, he likes the curves and a well-fed body) and of course Usopp likes Sanji's hands and legs.
Development: Nuance Pre-time skip, full development Post-Time skip.
Love language: Acts of service, physical touch (heavily). Technically all love languages they can use but the first two are the main ones.
Negative: Insecurity and self esteem for both can end in miscommunication and mutual hurt without realising (internal homophobia).
Zoro: Confident, arrogant
Usopp: Hard-working, pessimistic
Things in common: Care for the crew. His dreams are not physical but an abstract goal, and only they will reach it once they themselves acknowledge it. Sometimes hide their emotions for the greater of good.
Tropes: Friends to lovers. Grumpy vs sunshine. Slow burn. Definitely drunk buddies (example: Dressrosa allies' cheering scene). Teasing each other (like pretime skip shenanigans)
Other headcanons: First kiss. First relationship. Usopp confess first. Demiaro Zoro and Pan demi Usopp.
Development: Early Pre-time skip, stops for a while, fully development later in Post-Time skip
Love language: Physical touch & quality time.
Negative: Lack of words can affect Usopp self esteem unless they work in a mutual way of reassurance.
Ace: Adventurous, Hot-headed
Things in common: Self-esteem issues. Daddy issues. The inexplicable feeling to demonstrate something to the world.
Tropes: Best friend's brother. Funny guy x hot guy. The-what-could-have-been-couple.
Other headcanons: Tiny silly crush. Usopp artistic side captivates Ace's attention because he likes how he pictures life beautiful landscapes and turn every emotion, even negatives (especially those) into art.
Development: Slight Pre-time skip
Love language: Quality time.
Negative: Not talking about their emotions and problems. Fate.
Sabo: Chivalrous, unhinged
Usopp: Joyful, perfectionist
Things in common: Like fairytales and stories. Dreamers.
Other headcanons: Kisses on the scars and burns. Teach each other dialect and idioms (a little bit of language barrier with the different level of vocabulary). Also a little bit of love at first sight after battle. Pansexual Usopp x Graysexual Sabo
Development: Post-time skip. Dressrosa first meet.
Love language: Quality time and words of affirmation.
Negative: Long distance relationship.
Eustass Kid: Loyal, feral, stubborn
Usopp: Versatile, Sassy, insecure
Things in common: Like mechanics stuff. Inventors. Same music taste. Unique fashion style. Like Tattoos.
Tropes: Size difference, grumpy vs sunshine. Fast burn. Enemies to lovers.
Other headcanons: Balance each other emotions. Opposites attract. Pan x Pan. Scars bonding. Usopp paints tattoos on Kid.
Development: Later Post-time skip.
Love language: Physical touch, words of affirmation and unexpectedly acts of service (remember when Kid got out of the cell and comeback without caring if he was captured again because of his nakama? gotta give him credit for that)
Negative: Kinda doomed relationship, they are in enemies pirates crew. Long distance relationship. Too much angst. Different personalities and ideologies. Tension because neither of them will give in.
Law: Analytic, bottled-up
Usopp: Down-to-earth, sceptical
Things in common: like superheros stories. Hide certain emotions. Tattoos conversations.
Tropes: Slow burn. Strangers to lovers. Forced proximity. Age gap. Nerd x nerd.
Other headcanons: In a ship with crazy people they find middle ground in each other and a comfort space to rest. Sometimes gazes can have their own language.
Development: Early Post-time skip
Love language: Quality time and a little of words of affirmation.
Negative: Long distance relationship. Generational differences.
