Disney Jessie Series Wiki


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Characters Shipped

Jessie Prescott and Tony Chiccolini


In love with
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." in a romantic way and a smile.
  • Jessie replies by saying 'I'm Jessie.' with a smile and 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 with all of her shopping bags.
  • Though Tony claims he was attempting to be 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 asked about it, he denied it.
  • Tony grabs an umbrella for Jessie when it started raining, later saying that she looked so pretty with the raindrops in her hair.
  • Tony tells Jessie she's the prettiest guy he's ever seen, when Jessie tells him to treat her like she's just one of the guys.

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!" before Luke responds with "I know, right?".
  • He wanted to warn Jessie that the music producer was just 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 Brody is cheating on Jessie with another girl)
  • When Brody calls Tony "doorman", Jessie stands up for him and says, "the doorman's name is Tony". Jessie tells Brody Tony's more of a gentlemen than he'll ever be and dumps him.
  • Jessie tells Tony he smells nice, kind of lemony.
  • At the end, 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 appologised 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 first date.

Tempest in a Teacup

  • Jessie knits Tony a wool scarf.
  • Jessie and Tony go on their fourth attempted date.
  • When Jessie came out of her room Tony said "Wow! You look Wow!"
  • Tony did not laugh when Jessie got soaked.
  • Tony offered her his jacket when Jessie got soaked.
  • Jessie said that she looked ridiculous, but Tony disagreed and said she looks beautiful.
  • Tony kissed Jessie. At the end of the kiss, she looks like she wants to kiss him again because of her puckered lips.
  • In the end, Jessie and Tony dance together. They grab hands.
  • At the end, Tony said that he and Jessie are together by saying 'we had a few bumps in the road, but were 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 mentions if he ever saw 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 the noodles in his face in an attempt to show his love for Jessie.
  • When watching a movie under the stars in the park they almost kiss but then Officer Petey interups.

The Trouble with Tessie

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

    Tessie in "Why Do Foils Fall In Love?"

  • Tony wants Jessie to meet with his parents.
  • He takes her to a fancy italian restaurant, which is 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 she doesn't want to get married for years and years and Jessie looks hurt meaning that she does want to marry Tony in the future.

Why Do Foils Fall In Love?

  • Jessie tells the Ross' 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 and she was very happy. 

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 shared a passionate hug. 

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.
  • Their hug was the same as the types they had when they were dating.
  • 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 his feelings and almost did
  • Jessie thanked Tony for helping Brooks and smiled at him
  • When Brooks proposed to Jessie, Tony looked heartbroken and left in the elevator.


  • 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.
  • It was rumoured that they would get married in Season 3. Although, it might not happen.

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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