Disney Jessie Series Wiki


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Characters Shipped

Jessie Prescott and Tony Chiccolini


Still In Love With Each Other
Best Friends
Exes (Break-Up and Shape-Up)



Portrayed By

Debby Ryan and Chris Galya

Tessie (T/ony and J/essie) is the ex-relationship between Jessie Prescott and Tony Chiccolini. They met in the episode, New York, New Nanny, and Tony has been helping Jessie in any way possible throughout the show. They decided to break up, but stay as best friends, in Break-Up and Shape-Up.

Tessie Moments

New York, New Nanny

  • Tony helps Jessie up after she falls over from being pushed out of the cab.
  • Tony falls for Jessie as soon as he meets her.
  • Tony says "I'm Tony." and smiles in a possibly romantic way.
  • Jessie replies by saying 'I'm Jessie.' with smilling in a romantic way.

Used Karma

  • Jessie and Tony go on a date at the central park.
  • Tony admitted to Zuri that he was trying to kiss Jessie when she comes down to get the mail.
  • Tony gives Jessie a "Welcome to New York, Forgetta basket".
    Glue dunnit - tony & jessie
  • Tony helps Jessie carry her shopping bags.
  • Though Tony claims he was attempting to be only friends with Jessie the entire time, he later changes his mind.
  • Tony tells Jessie he had a good time with her.
    Glue dunnit - jessie & tony
  • Tony calls Jessie pretty and smiles.
  • Tony wanted to kiss Jessie, but when she later asked about it, he denied it.
  • Tony grabs an umbrella for Jessie when it started raining, later saying that she looked pretty with raindrops in her hair.
  • Jessie tells tony to treat her like she's "just one of the guys", and Tony responds by telling her she is the prettiest guy he's ever seen.

One Day Wonders

  • Tony wants to go into Jessie's room (along with everyone, excluding Bertram) , and when Jessie says no, he turns to Luke and says "Can't blame a guy for trying!".
  • He attempted to warn Jessie that the music producer was ripping her and Luke off.

The Princess and the Pea Brain

  • At the very beginning of the episode, Tony tries to impress Jessie by showing her a trick on his new dolley.
  • Tony is shown to be jealous when Brody Winton asks out Jessie.
  • In the story that Zuri is telling Jessie, Tony admits that he's fallen in love with the princess, who is Jessie.
  • In Zuri's story, Tony tries to become irresistable so he can win Jessie's (the princess) heart.
  • Tony describes all the things he loves about her ("smart", "pretty", "always smells nice") to Brody, and is overheard by Jessie, who is being cheated on by Brody.
  • Tony stands up to Brody and tells him he doesn't deserve a girl like Jessie (due to the fact that he was cheating on her).
  • When Brody calls Tony "doorman", Jessie stands up for him and says, "the doorman's name is Tony".
  • Jessie tells Brody that Tony's more of a gentlemen than Brody will ever be and dumps him.
  • Jessie tells Tony he smells nice, "kind of lemony".
  •  Tony wants to ask Jessie out on a date, and Jessie agrees to go on a date with Tony.

Glue Dunnit: A Sticky Situation

  • They try to go out on their second first date.
  • Jessie apologised to Tony for missing their second first date.
  • Jessie thought that Tony was going to kiss her.
Jessie 2

Tessie about to kiss.

Evil Times Two

  • They try to go out on their third attempt at a first date.

Tempest in a Teacup

  • Jessie knits Tony a wool scarf.
  • Jessie and Tony go on their fourth attempt at a first date.
  • When Jessie came out of her room, Tony said "Wow! You look Wow!"
  • Tony did not laugh when Jessie got soaked.
  • Tony offered Jessie his jacket.
  • Jessie said that she looked ridiculous, but Tony disagreed and said she looked beautiful.
  • Tony kissed Jessie.
  • In the end, Jessie and Tony dance together.
  • They hold hands.
  • Tony said that he and Jessie are together despite the problems, saying "we had a few bumps in the road, but we're together".

Season 2 Moments

Green Eyed Monsters

  • For the entire episode, Tony was jealous of Jessie spending more time with Petey than with him.
  • When Emma asked him if he had ever seen the way Jessie eats BBQ, he repiled, "I sure have!" in a happy tone,
    Tumblr mcmhts4QZH1rojgmbo10 1280

    Tony and Jessie about to kiss in Green-Eyed Monsters

    suggesting that he loves the way she eats.
  • As soon as Jessie tells Tony that Petey is going to be at her improv performance, he immediately suggests that he join the both of them as well, once again hinting at jealousy.
  • Tony angrily shouts a suggestion for a setting during the improv performance at the noodle cafe, and his idea was a "girlfriend stealing cop".
  • Tony displays even more jealousy as he watches the improv performance with Jessie and Petey, and he appears to be shocked as they start getting closer to each other.
  • Tony marches right up to Officer Petey, and chucks noodles in his face out of jealousy.
  • When watching a movie under the stars in the park, they almost kiss, but Officer Petey interrupsthem.

The Trouble with Tessie

  • Tony makes Jessie a Tessie T-shirt with both of their faces on the front of it.

    Tessie in "Why Do Foils Fall In Love?"

  • Tony tells Jessie he wants her to meet with his parents.
  • He takes her to a family style Italian restaurant owned by his parents.
  • Jessie thinks that he is about to propose to her.
  • Jessie says that, while she is flattered, she does not want to rush into things with Tony.
  • Tony says he doesn't want to get married for years and years.
  • Jessie looks offended.

Why Do Foils Fall In Love?

  • Jessie tells the Ross kids that it's their first anniversary.
  • Jessie wanted to write a love song for Tony.
  • Emma thought it was romantic that Jessie wanted to write a song for Tony.
  • Jessie was very hurt when she thought that Tony had forgotten their anniversary.
  • When Tony came into the Ross penthouse the following day, he said, "Hey, Jessie. Happy anniversary!" to her.
  • When Jessie realised she got the day wrong, she felt awful and thought Tony would be very mad at her.
  • Jessie wanted to make sure the song was perfect for Tony. 
  • The title of the song is 'Best Year of My Life' showing she loves Tony.
  • When Jessie was singing to Tony, he joined her on the stage.
  • Near the end of the song, Tony wrapped his arms around her.
  • After Jessie performed, Tony kissed her head. 

Break-Up and Shape-Up

  • At the beginning of the episode, they talk about what they're going to do with each other that Saturday.
  • Tony got jealous of the time Jessie was spending with Ted and Jessie got jealous of the time Tony was spending with Vic.
  • When Jessie saw that her ex-boyfriend Ted looked completely different, she wanted Tony to see him in the lobby and get jealous.
  • Tony told Jessie that he would always love her and Jessie responded by telling him that she would always love him too.
  • Jessie and Tony agreed to stay friends after they broke up and hugged one another. 

Season 3 Moments

The Blind Date, the Cheapskate, & the Primate

  • Jessie and her kids walk up the service stairs to avoid Tony.
  • They both set each other up on blind dates.
  • Jessie looked jealous when Tony said that his date is the most beautiful girl he had ever seen.
  • Tony thought Jessie wanted to date him.
  • Jessie said it was sweet that Tony thought that she was the girl he was going to go on a date with and said "Oh, Tony, you're not over me. That's so sweet."
  • Tony apologized to Jessie for the disastrous date with Earl.

Lights, Camera, Distraction!

  • Jessie was doing a movie about their relationship, for a film festival.
  • Tony didn't hesitate about playing Jessie's boyfriend for the movie
  • Jessie was happy when Tony said he would be happy to play himself.
  • They had to do the kiss scene from Tempest in a Teacup.
  • Jessie said the kiss scene was the most important scene of the movie, implying she liked kissing Tony.
  • They both agreed that it was awkward for having to kiss each other now that they're broken up.
  • Jessie was worried that she may have ruined her friendship with Tony.
  • When Jessie entered the building, they smiled at each other.
  • Tony apologized to Jessie for letting her down, after quitting her movie.
  • Jessie told Tony her movie won the film festival.
  • Tony congratulated Jessie.
  • They hugged.
  • They both awkwardly pulled away from each other.
  • Tony wanted to do a sequel to her movie, and was happy to play Jessie's boyfriend.

No Money, No Problems

  • Tony realized he still had feelings for Jessie
  • Tony was jealous of Jessie's relationship with Brooks.
  • After being out for a while, Jessie walked into the building and said "hi" to Tony, whilst smiling
  • Tony went into the elevator with Jessie
  • Tony said he's been thinking about Jessie a lot recently.
  • Tony wanted to tell Jessie about his feelings for her.
  • Jessie thanked Tony for helping Brooks and smiled at him.
  • When Brooks proposed to Jessie, Tony looked heartbroken and left in the elevator.

There Goes the Bride

  • Jessie walked up to Tony and had a big smile on her face
  • Jessie invited Tony to her wedding
  • Jessie said that Tony is a very important person in her life
  • Tony said he'd love to attend Jessie's wedding
  • Tony visits Jessie in her bedroom
  • Tony gives Jessie a wedding gift
  • Tony said that Jessie was his favourite member of her inprov debut.
  • Jessie said it was incredibly thoughtful of the gift and thanked Tony with a smile
  • They shared a pashionate hug
  • When pulling away, they looked into each other's eyes as if they were about to kiss
  • Tony offered to do Jessie's wedding and she said it would be incredible.
  • Emma hoped the present would be a kiss.
  • Brooks thought she said she can't marry him because of Tony.
  • Jessie said it is partly because of it, hinting she still has feelings for Tony.


  • The episode called The Trouble With Tessie was named after the pairing.
  • Mrs. Chesterfield has called Jessie, Tessie multiple times.
  • The term Tessie was only mentioned twice on the show.
  • Jessie made a song about Tony going out bowling instead of going out for their anniversary.
  • Jessie wrote a romantic song for Tony and performs it to him for their anniversary called 'Best Year Of My Life'.
  • They broke up in Break-Up and Shape-Up, but agreed to stay friends.
  • They will most likely get back together in Season 4

Start a Discussion Discussions about Tessie

  • dating

    3 messages
    • Jessie and Tony are dating... which you would know if you actually payed attention to the plot of the series... 
    • hahaha #tessie =]

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