This article details the various close relationships explored throughout Pooh's Adventures and other spin-offs, including best friends, romances, student-teacher relationships, rivalries, arch-eneimes and family relationships

Best friendships

Winnie the Pooh and co./Ash, Misty, and Brock

Winnie the Pooh, Piglet, Tigger, Rabbit, and Eeyore traveled to the Pokémon World to look for an old friend of Christopher Robin's Ash Ketchum and met him along his friends Pikachu, Misty and Brock in Pooh's Adventures of Pokémon The Movie: I Choose You! and Pooh's Adventures of Pokémon: The First Movie. And together they went to New Island and put a stop to Mewtwo's evil plan until he is redeemed by Ash's actions. Since then Ash and Pikachu have reunited with them when they joined the the Chinese Imperial Army in Pooh's Adventures of Mulan. Now he and Misty and Brock formed a strong bond with Pooh and his friends and go on many adventure together during their Pokémon journey. Ash shows very protective to Pooh and his friends. Tigger loves to play with Pikachu and finds him funny. Misty is very fond with Piglet. Rabbit and Brock show each other a great respect but much to Rabbit and Misty's annoyance Brock can always shows his "way" with girls. Ash and his friends always gave Eeyore's comfort when he's always and gets along with him.

Winnie the Pooh and co./Lincoln and his sisters

Winnie the Pooh and co./Littlefoot and his friends

Winnie the Pooh and co./Tino, Lor, Carver, Tish

Winnie the Pooh and co./Simba

Winnie the Pooh and co./Timon and Pumbaa

Timon and Pumbaa are good friends of Pooh, Piglet, Tigger, Rabbit, and Eeyore. It appears that they get along we with Timon and Pumbaa quite well as they help them take care Simba when he was a cub. Since then, Timon and Pumbaa goes on their own adventures and sometimes join Pooh and the gang on their adventures.

Winnie the Pooh and co./The Digidestined

Winnie the Pooh and co./The Mane Six

Winnie the Pooh and co./Thomas the Tank Engine and his friends

Winnie the Pooh and co./SpongeBob SquarePants and his friends

Winnie the Pooh and co./Alex and his friends

Winnie the Pooh and co./Skipper, Kowalski, Rico and Private

Winnie the Pooh and co./Lightning McQueen

Winnie the Pooh and co./Mater

Winnie the Pooh and co./Cruz Ramirez

Winnie the Pooh and co./Aladar and his family

Winnie the Pooh and co./Green Ranger

Winnie the Pooh and co./Korra and her friends

Winnie the Pooh and Mickey Mouse

Sora, Donald, Goofy, and Power Rangers

Woody Woodpecker and Ttark

Ash Ketchum and Hiro (T&F)

Lightning McQueen and Dusty Crophopper

Ariel and Littlefoot

Twilight Sparkle and Skipper (The Penguins of Madagascar)

Tino Tonitini and Squire Flicker

Pappy Polie, Uncle Gizmo, Pollie Pi, Karen Rooney and McKenzie Fox

Olie Polie and Billy Bevel

Aqua, Terra and Ventus

Cyd Ripley and Shelby

Sonic the Hedgehog and Rainbow Dash

Fluttershy and Cream the Rabbit

Lilo Pelekai and Cream the Rabbit

Mario and Sonic

Tails and Luigi

Peach and Amy Rose

Ash Ketchum & Yugi Moto

Ash Ketchum & Seto Kaiba

Yugi Moto and Lilo & Stitch

Yugi Moto and Gladion

Sector V Kids Next Door and Powerpuff Girls

Lilo's Ohana and Power Rangers

Tomax Oliver and Sora, Donald & Goofy

Tomax Oliver & Mickey Mouse

Tomax Oliver & Sonic Heroes

Tomax Oliver & Lilo's Ohana

Spider-Man & Black Cat

Spider-Man, Black Cat, and The X-Men

Aisling and Moonlight Shimmer

Ash Ketchum & Lightning McQueen

Ash Ketchum & Miguel Rivera

Ash and Miguel are best friends. Throughout the movie, Ash teaches Miguel that family always comes first. He also teaches the Rivera family that the power of music, love and forgiveness can lead to unexpected results. At the end of the movie, the Riveras blessed Ash's wisdom and he and his friends are always welcomed to them.

Romantic relationships

Mewtwo and The Good Fairy

Bowser and Mistress 9

Bowser Junior and Ranamon

Bowser Junior and Azula

Darth Maul & Azula

Ash Ketchum & Serena

Ash Ketchum & May

Ash Ketchum & Dawn

Ash Ketchum & Lillie

Cilan & Mallow

Spectra Phantom & Misty

Richie and Rini

Tino Tonitini and Sunset Shimmer

Boba Fett and Moonlight Shimmer

Zordon and Palutena

Austin Moon & Ally Dawson

Lela & Tanner

Rapunzel & Flynn Rider

Aqua & Ventus

Dez Wade & Carrie

Li Showron & Sakura Avalon

Li Showron & Lilo Pelekai

Stitch & Angel

Tomax Oliver & Elena Validus

Mario & Peach

Luigi & Daisy

Gonzales Mario & Rosalina

Sonic & Amy

Sonic & Sally

Tails & Cosmo

Shadow & Cream

Shadow & Rouge

Torque & Lilac

Numbuh 4 & Numbuh 3

Numbuh 1 & Numbuh 362

Numbuh 2 & Numbuh 5

Numbuh 274 & Violet Parr

Ben Valorheart & Twilight Sparkle

Soarin & Rainbow Dash

Dexter & Blossom

Scorpio (Experiment 627) & Vivian

Tommy Oliver & Kimberly Hart

Zack Taylor & Trini Kwan

Inuyasha & Kagome

Miroku & Sango

Shippo & Nina Tucker

Edward Elric & Winry Rockbell

Buster & Babs Bunny

Plucky Duck & Shirley the Loon

Hamton J. Pig & Fifi La Fume

Hamton J. Pig & Priscilla Pig

Naruto Uzumaki and Hinata Hyuga

Naruto Uzumaki and Misaki Suzuhara

Sasuke Uchiha and Sakura Haruno

Korra and Mako

Ben Tennyson & Julie Makimoto

Kevin Levin & Gwen Tennyson

Seto Kaiba & Kikyo

Mokuba Kaiba & Hatoko Kobayashi

Littlefoot & Ali

Drew & Miette

Mickey Mouse & Minnie Mouse

Donald Duck & Daisy Duck

Goofy & Clarabelle Cow

Goofy & Sylvia

Oswald the Lucky Rabbit & Ortensia the Cat

Max Goof & Roxanne

Phineas & Isabella

Trent & Gwen

Duncan & Courtney

John Smith & Pocahontas

John Rolfe & Pocahontas

John Rolfe & Clair

Bentley & Penelope: What happened in Sly Cooper: Thieves in Time is outrageous, intolerable and absolutely unnecessary! Penelope should NOT have become a villain in the first place! For that, I am seeing to it that Bentley and Penelope are brought back together! 

Ragna the Bloodedge & Serenity Wheeler

Ichigo Kurosaki & Orihime Inoue

Renji Abarai & Rukia Kuchiki

Spider-Man & Mary Jane Watson

Student-Teacher relationships

Mewtwo and Master Splinter

Ahsoka Tano and Darth Vader

Elsa and Darth Vader

Aisling and Darth Vader

Power Rangers and Zordon

Pit and Palutena

Ninja Turtles and Master Splinter

Batman and Darkwing Duck

Batman and Green Ranger

Mewtwo and Korra

Darth Vader and Zordon

Qui Gon Jinn and Obi Wan Kenobi

Kanan Jarrus and Ezra Bridger

Twilight Sparkle and Starlight Glimmer

Shadow the Hedgehog and Master Splinter

Aang and Lilo Pelekai

Zuko and Lilo Pelekai

Katara and Lilo Pelekai

Toph Beifong and Lilo Pelekai

Goku & Sonic the Hedgehog

Vegeta & Shadow the Hedgehog

Trunks Briefs & Silver the Hedgehog

Yugi Moto & Ash Ketchum: Yugi would teach Ash how to play Duel Monsters.

Riku & Tomax Oliver: Riku would naturally help Tomax to control powers of darkness, so that Tomax can be able to wield the Sword of Darkness easily without being corrupted.

Rivalry relationships

Scrooge McDuck and Mr. Krabs

Gmerl and Philmac

Ash Ketchum & Alain

Ash Ketchum & Gladion

Ash Ketchum & Yugi Moto

Yugi Moto & Seto Kaiba

May & Drew

Serena & Shauna

Shauna & Miette

Goku & Vegeta

Sonic & Shadow

Sonic & Rainbow Dash

Rainbow Dash & Lightning Dust

Mewtwo and Infinite (Sonic Forces)

Mewtwo and Shadow the Hedgehog

Arch-Enemies relationships

Bowser and Zordon

Mewtwo and Bowser

Aisling and Bowser Junior

Good Fairy and Mistress 9

Mewtwo and Jafar

Korra and Azula

Tigger and Shere Khan

Rainbow Dash and Starscream

Brian Griffin and the Dazzlings

Peter Griffin and Ernie the Giant Chicken

Sora and Lord Zedd

Gustavo and Hawk

Sasuke Uchiha and Lord Zedd

Emerl and Primus Onslaught 

Philmac and Terios 

Mark EVO and Chaos Emerl Replica

Philmac and Primus Onslaught

Family relationships

Misty and Cinderella

Starlight Glimmer and Lightning McQueen

Mistress 9 and Ghetsis

Ash Ketchum and April O'Neil

The Digidestined and the Mighty Morphin Power Rangers

Kitty Katswell and Hanah Streaker

Ginger Grant and Liv Rooney

Bowser and Dark Specter

Bowser Junior and the Koopalings

Gladion and Lillie

Donald Duck, Daisy Duck, Scrooge McDuck, Huey, Dewey, Louie and Webby

Cream the Rabbit and Judy Hopps: Judy is Cream's favorite aunt, and Cream is Judy's beloved niece.

Judy Hopps and Buttercream Sunday

Twilight Sparkle and Nyx

Seto Kaiba, Kikyo, Mokuba Kaiba and Roku Kaiba (formerly known as Six)

Littlefoot and Dink (both characters are cousins)

Rabbit and Mr. Herriman

Misty and Frankie Foster

Ashi and Aisling

Ashi and Mewtwo: Mewtwo is Ashi's adopted father. While he's not romantically in love with the Good Fairy, they both agreed to raise her just like how they do with Aisling.

Ashi and Good Fairy: The Good Fairy is Ashi's adopted mother. While she's not romantically in love with Mewtwo, they both agreed to raise her just like how they do with Aisling.

Ashi and Zordon