Out of all The Chipmunks and Chipettes, Theodore and Eleanor are the most open couple. They both share similar interests. Plus, several moments throughout the franchise hint towards Eleanor having a large crush on Theodore. Similarly, Theodore commonly gets nervous or blushes when he is near her, volunteering to help her more than anybody else. Both may, for now, experience puppy love for each other, but it will soon grow into true love.
80s Series & Films
- In The Chipettes, Theodore tells Eleanor that he also eats when he's nervous when he sees her eating plastic fruit, and when she faints and falls backwards, he quickly catches her.
- In I Love The Chipmunks Valentine, Theodore makes Eleanor cookies with hearts on them for Valentine's Day.
- In Soccer to Me, Theodore hugs Eleanor after her soccer game against Alvin.
- In Big Dreams, on both potential future sequences, they are shown being married happily regardless of economic status. They also dance together in "Everybody Have Fun Tonight."
- In Help Wanted: Mommy, Theodore puts his arm around Eleanor before they walk off.
- In May the Best Chipmunk Win, Theodore excitedly calls out Eleanor's name when she and her sisters enter their new classroom. He takes her hand and guides her to her new seat.
- In Operation Theodore, Theodore brought Eleanor her homework.
- In The Brunch Club, Theodore helps Eleanor up when she falls down and holds onto her hand while smiling at her.
- In the Hardee's Glass Commercial, Theodore and Eleanor dance together.
- In Alvin and the Chipmunks Meet the Wolfman, Theodore blushes while giving Eleanor a necklace.
- In The Chipmunk Adventure, they dance together during "The Girls of Rock 'n' Roll."
- In The Chipmunk Adventure, the six kids are all in the same hot air balloon and coming close to landing back home and to their horror they turn to see a large airplane flying right towards them. For a brief moment Theodore is seen putting both hands on Eleanor's shoulders right before the wing of the plane knocks into their balloon basket, perhaps it was a small attempt on his part to try and protect her.
- In Alvin and the Chipmunks: The Squeakquel, Theodore develops a crush on Eleanor when he meets her at the lockers.
- In Alvin and the Chipmunks: The Squeakquel, he is still dazed after his first encounter with Eleanor as he calls her a "beautiful, green gumdrop."
- In Alvin and the Chipmunks: The Squeakquel, Theodore catches Eleanor when she stumbles in her high-heeled sandals. Theodore points them out to her. He then confesses to her that he thinks she looks great just the way she is. When she asks him if he really meant it, he shyly confirms it.
- In Alvin and the Chipmunks: The Squeakquel, when Eleanor says it is a great honor to sing with them, he says, "For you or for us?", confirming he was equally happy to perform with her, also they dance together in "we are family."
- In Alvin and the Chipmunks: The Squeakquel, Theodore says goodnight to Eleanor.
- In Alvin and the Chipmunks: Chipwrecked, they briefly dance together during "Vacation."
- In Alvin and the Chipmunks: Chipwrecked, while they are oil-skating on the deck, Theodore grasps Eleanor's paws and they spin each other around.
- In Alvin and the Chipmunks: Chipwrecked, after Eleanor falls off the zip line, Theodore is seen to be right by Eleanor's side, helping her up.
- In Alvin and the Chipmunks: Chipwrecked, while Eleanor sits on the sidelines watching Simone and Jeanette dance, Theodore walks over and asks her if she would like to dance with him. She accepts happily, giggling and throwing her crutches aside.
- In Alvin and the Chipmunks: Chipwrecked, Theodore and Eleanor can be seen singing and dancing together and at the end of "Born This Way/Ain't No Stoppin' Us Now/Firework" they wave to the crowd while holding hands.
- In Alvin and the Chipmunks: The Road Chip, he and Eleanor dance together at the party.
- In A Room of One's Own, Theodore talks to Eleanor when he misses Alvin.
- In Secret Admirer, when the Chipmunks think that Kevin has a crush on one of the Chipettes, Theodore is worried that it's Eleanor but takes it back, hinting he's nervous at the thought of Kevin taking her as his 'girlfriend.'
- In Secret Admirer, the fact that Theodore has a crush on Eleanor is heavily implied throughout the episode as he showed to have interest in her, and he and his brothers followed The Chipettes around school, only to see them 'flirting' with Kevin. Even at the end of the episode The Chipmunks denied any feelings they had for The Chipettes.
- In The Chipmunk and the Catfish, Theodore holds Eleanor's hand and begs for her help.
- In Ballet Boys, Theodore likes the compliment Eleanor says about him that wearing a skirt is awesome.
- In The Great Chipmunk Detective, Theodore is eager to help Eleanor.
- In Tour Bus, Theodore is flattered when Eleanor calls him a genius, unaware that she was being sarcastic.
80s Series & Films
- In The Chipettes, Eleanor offers Theodore breakfast.
- In The Greatest Show-Offs on Earth, Right after Eleanor steals Theodore's last peanut from his peanut bag; she smiles and hugs onto his arm, while he glares at her for eating his last peanut on him.
- In Island Fever, they hug each other when they get scared and Eleanor comforts Theodore when he gets upset.
- In Snow Wrong, Theodore trips and Eleanor catches him.
- In The Gang's All Here, Eleanor saves Theodore from those bullies at the roller skate rink by picking him up and skating away with him.
- In numerous episodes, Eleanor has a picture of Theodore in her room.
- In The Chipmunk Adventure, Eleanor kisses one of the Theodore dolls right after she and Jeanette rescue Brittany from the shark that attacked her.
- In I Love The Chipmunks Valentine Special, she made a heart-shaped cake for Theodore with his name on it and stared at his picture dreamily talking about wanting it to be perfect. She is also Theodore's date for the dance.
- In Alvin and the Chipmunks Meet the Wolfman, Eleanor shows concern for Theodore when he is getting bullied by Nathan. Eleanor smiles when she talks about how they can act together and when Theodore is a werewolf Eleanor misses how he was before.
- In Alvin and the Chipmunks: The Squeakquel, Eleanor eagerly asks, "So, when do we meet the Chipmunks?". However, when Ian lied and said that The Chipmunks cannot be trusted, she said, "But not Theodore, right?" Ian disagreed, making Eleanor sigh in sadness and hurt. This also confirms that, even though she was eager to meet the whole group, Theodore was the only one she truly cared about.
- In Alvin and the Chipmunks: The Squeakquel, after they meet the Chipmunks, she said to Brittany, "I think Theodore was looking at me!," showing she had a crush on Theodore and that she was ecstatic he had noticed her in return. When Brittany reminded her and Jeanette that Ian said they couldn't trust them, Eleanor looked visibly hurt.
- In Alvin and the Chipmunks: The Squeakquel, Ms. Ortega notices Theodore is depressed and asks if Eleanor would help him wrap presents. Eleanor smiles at him, eagerly accepting to work with him. When Theodore compliments her, she smiles at him, touched.
- In Alvin and the Chipmunks: The Squeakquel, when reunited with The Chipmunks, she walks over to hug Theodore.
- In Alvin and the Chipmunks: The Squeakquel, Eleanor says, "This is such an honor!," happy to be able to perform with him and his brothers.
- In Alvin and the Chipmunks: The Squeakquel, the two of them say good night to each other at the end of the film.
- In Alvin and the Chipmunks: Chipwrecked, while Eleanor is watching Simone and Jeanette dance in the rain, she says sadly how fun it looks as she is on crutches. Theodore looks over at her sadly and walks over to her side. He asks her to dance and she accepts happily, throwing away her crutches.
- In Alvin and the Chipmunks: Chipwrecked, when Theodore and Eleanor are being carried across the bridge by Zoe, Eleanor holds on to Theodore and covers his eyes knowing that he was scared.
- In Alvin and the Chipmunks: Chipwrecked, Eleanor made a Jungle Monster costume for Theodore on the plane out of one of the barf bags.
- In Alvin and the Chipmunks: The Road Chip, Eleanor called Theodore "Theodorable," a pun on Theodore's name and adorable.
- In A Room of One's Own, Eleanor comforts Theodore when he misses Alvin.
- In Good Luck Mr. Whiskers, Eleanor comforts Theodore when he's scared about a "cat curse."
- In Ballet Boys, Theodore wanted to wear a tutu for the class because Eleanor told him that he looked "awesome" in it.
- In Lost in Space...Camp, Eleanor defends Theodore when he’s being picked on.
- In Addicted, Eleanor seems concerned about Theodore whose acting odd when she see him talking to the cupcakes and even named them as well; she even asked her Jeanette if anyone has gone "insane" from the test, then when Theodore failed the test it was Eleanor who grabbed him by his hoodie before dragging him out of the room.
- In Tour Bus, Eleanor demanded to know which "genius" decided to bring along the big beanbag chair and was clearly being sarcastic when using the word "genius"; Theodore who didn't know that it was sarcasm proudly exclaimed "ME!", before turning to Alvin and happily saying to him "She thinks I'm a genius."
- They both have a love for food and are very talented in the kitchen.
- Both of their colors are a tone of green.
- They happen to be the "chubbiest" of their respective groups of three.
- Both were voiced by Janice Karman in the 1980's animated series. In the CGI/live-action films, Karman still does both of their singing voices.
- They are the shortest of the six.
- They both share names with famous Roosevelts.
- They get stuck in tight spaces due to their size in Alvin and the Chipmunks: The Squeakquel: Theodore in a cage in the zoo and Eleanor in the mail slot of an apartment complex.
- In the CGI/live-action versions, they have the lightest shade of fur out of their siblings.
- In the CGI/live-action versions, they have green eyes.
- Both are very forgiving and are unlikely to hold a grudge.
- They are the most optimistic and bubbly.
- In Alvin and the Chipmunks: The Squeakquel, both receive rude comments about their weight: Theodore by the jocks and Eleanor by Ian.
- They are the youngest of their siblings.
- He has trouble standing up to Alvin when he forces him into situations.
- Theodore is not very athletic.
- Theodore is quieter and is less likely to speak out.
- He is sometimes shown to act irrationally when his feelings are hurt. For example, he goes out to look for a new family at the zoo when his brothers are fighting in Alvin and the Chipmunks: The Squeakquel.
- He can be a bit naive at times.
- She stands up to Brittany (or anyone else, for that matter) easily.
- She is more athletic than Theodore, especially in the 80s incarnation, as she was shown to have an interest in soccer and swimming during the cartoon series.
- Eleanor is more outspoken, unafraid to voice her views.
- She is very level-headed, thinking things through before acting.
- While still innocent in comparison to her sisters, she is actually pretty mature, perhaps even in comparison to her sisters and especially in Theodore.