Characters Shipped

Jessie Prescott and Tony Chiccolini


Best Friends
In Love



Portrayed By

Debby Ryan and Chris Galya

Tessie (T/ony and J/essie) is the 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. They got back together in The Ghostest With the Mostest.

Tessie Moments

Season 1 Moments

New York, New Nanny

  • Tony helps Jessie up after she falls over from being pushed out of the cab.
  • Tony says "I'm Tony," and smiles as if he is interested in her.
  • Jessie replies by saying "I'm Jessie," while smiling.

Used Karma

  • The ex-couple goes on a date at the central park.
  • Tony admits to Zuri that he was trying to kiss Jessie when she came down to get the mail.
  • When Tony was about to kiss Jessie, he played it off by saying he was only going to reach for his jacket.
  • 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.
  • 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.
  • Tony tells Jessie he had a good time with her.
    Glue dunnit - jessie & tony
  • Tony calls Jessie pretty and smiles.
  • Tony grabs an umbrella for Jessie when it starts raining, later saying (to Zuri as he talked about Jessie and his attempt to kiss her) that she looks pretty with raindrops in her hair.
  • Tony wants to kiss Jessie, but when she later asks about it, he denies it.

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 attempts to warn Jessie that the music producer is 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 dolly.
  • Tony tries to ask Jessie out, but, instead, says, "Hey, Jessie! I was wondering if you want to... have an apple?"
  • 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 irresistible so he can win Jessie's (the princess) heart.
  • Princess and pea brain - tony and ravi

    Tony with Sorceror Ravi, trying to find a way to impress Princess Jessie.

    Tony describes all the things he loves about her ("smart", "pretty", "nice", "always smells really, really good -- like one of those fancy air fresheners you plug into the outlet of the wall") 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 is 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 gentleman 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 apologizes to Tony for missing their second first date.
  • Jessie thinks that Tony is going to kiss her.

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 2

    Tessie about to kiss.

    Jessie and Tony go on their fourth attempt at a first date.
  • When Jessie comes out of her room, Tony says, "Wow! You look wow!"
  • Tony does not laugh when Jessie gets soaked.
  • Tony offers Jessie his jacket.
  • Jessie says that she looks ridiculous, but Tony disagrees and says she looks beautiful.
  • Tony kisses Jessie.
  • In the end, Jessie and Tony dance together.
  • They hold hands.
  • Tony says that he and Jessie are together despite many problems: "We had a few bumps in the road, but we're together."

Season 2 Moments

Green Eyed Monsters

  • For the entire episode, Tony is jealous of Jessie spending more time with Petey than with him.
  • When Emma asks him if he has ever seen the way Jessie eats BBQ, he replies, "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 his jealousy.
  • Tony angrily shouts a suggestion for a setting during the improv performance at the noodle cafe, and his idea is 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 interrupts them.

The Trouble with Tessie

  • Tony makes Jessie a Tessie T-shirt with both of their faces on the front of it.
  • 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 is their first anniversary.
  • Debby-ryan-jessie-why-do-foils-fall-in-love-picture-main-300x213

    Tessie in "Why Do Foils Fall In Love?"

    Jessie wants to write a love song for Tony.
  • Emma thinks it is romantic that Jessie wants to write a song for Tony.
  • Jessie is very hurt when she thinks that Tony has forgotten their anniversary.
  • When Tony comes into the Ross penthouse the following day, he says, "Hey, Jessie. Happy anniversary!" to her.
  • When Jessie realises she got the day wrong, she feels awful and thinks Tony will be very mad at her.
  • Jessie wants to make sure the song is perfect for Tony. 
  • The title of the song is 'Best Year of My Life', showing she loves Tony.
  • When Jessie is singing to Tony, he joins her on the stage.
  • Near the end of the song, Tony wraps his arms around her.
  • After Jessie performs, Tony kisses 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 gets jealous of the time Jessie is spending with Ted and Jessie gets jealous of the time Tony is spending with Vic.
  • When Jessie sees that her ex-boyfriend Ted looks completely different, she wants Tony to see him in the lobby and get jealous.
  • Tony tells Jessie that he will always love her and Jessie responds by telling him that she will always love him too.
  • Jessie and Tony agree to stay friends after they break up and hug one another. 

Season 3 Moments

The Blind Date, the Cheapskate, & the Primate

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

Lights, Camera, Distraction!

  • Jessie is doing a movie about their relationship for a film festival.
  • Tony doesn't hesitate about playing Jessie's boyfriend for the movie
  • Jessie is happy when Tony says he would be happy to play himself.
  • They have to do the kiss scene from Tempest in a Teacup.
  • Jessie says the kiss scene is the most important scene of the movie.
  • They both agree that it is awkward for having to kiss each other now that they're broken up.
  • Jessie is worried that she may have ruined her friendship with Tony.
  • When Jessie enters the building, they smile at each other.
  • Tony apologizes to Jessie for letting her down, after quitting her movie.
  • Jessie tells Tony her movie won the film festival.
  • Tony congratulates Jessie.
  • They hug.
  • They both awkwardly pull away from each other.
  • Tony wants to do a sequel to her movie and is happy to play Jessie's boyfriend.

No Money, No Problems

  • Tony realizes he still has feelings for Jessie
  • Tony is jealous of Jessie's relationship with Brooks.
  • After being out for a while, Jessie walks into the building and says, "Hi," to Tony, while smiling
  • Tony walks inside the elevator with Jessie
  • Tony says he's been thinking about Jessie a lot recently.
  • Tony wants to tell Jessie about his feelings for her.
  • Jessie thanks Tony for helping Brooks and smiles at him.
  • When Brooks proposes to Jessie, Tony looks heartbroken and defeated, leaving in the elevator.

There Goes the Bride

  • Jessie walks up to Tony and has a big smile on her face.
  • Jessie invites Tony to her wedding.
  • Jessie says that Tony is a very important person in her life.
  • Tony says he'd love to attend Jessie's wedding.
  • Tony visits Jessie in her bedroom.
  • Tony gives Jessie a wedding gift.
  • Emma and Zuri hope the present will be a kiss.
  • Tony says that Jessie is his favourite member of her improv debut.
  • Jessie says it was incredibly thoughtful of him for giving her a gift and thanks him with a smile.
  • Tony has a star made right next to her name.
  • Jessie jokingly says that he loves her name when she sees the star.
  • Tony, with an adoring look directed at her, says, "Absolutely," confirming that he still loves Jessie.
  • They share a long hug.
  • When pulling away, they look into each other's eyes as if they are about to kiss.
  • Tony offers to do Jessie's wedding and she says it will be incredible.
  • Tony threatens Brooks that he will not hesitate to hurt him if he doesn't treat Jessie right.
  • He calls Jessie an amazing lady.
  • Brooks thinks she said she couldn't marry him because of Tony.
  • Jessie says it is partly because of that, hinting she still has feelings for Tony, or doesn't want to leave him behind as he is her good friend.

Season 4 Moments

A Close Shave

  • Jessie has Tony pretend to be Brooks while Darla is visiting.
  • Jessie is annoyed that Tony struggles to remember his character, meaning she either doesn't want to give away the truth to Darla.
  • Jessie gets furious at Tony for accidentally hiring Darla at "his" (actually Brooks') alleged private school and tried to dissuade her from taking the job.
  • It is revealed that Jessie told Darla about Tony, and Tony waves his hair pleasantly upon finding this out.
  • Jessie looked jealous when Darla was gazing flirtatiously at "Brooks" upon finding out he and Jessie didn't get married.

The Ghostest With the Mostest

  • Tony told Jessie he wanted to get back together.
  • They shared a slow dance.
  • Tony waited for Jessie.
  • Jessie was surprised when she found out that Tony was the guy she was dancing with.
  • Jessie, unaware at first, said that Tony was her dream guy.
  • They hugged.
  • Tony said his dream came true because he finally had Jessie back.
  • They got back together.

Jessie Goes to Hollywood

  • They were in the lobby talking about their own problems to each other.
  • Tony surprised Jessie by showing up at LA. Jessie was really surprised to see Tony.
  • Tony told Jessie about his new job in LA.
  • They hugged.
  • Jessie was smiling after hugging Tony.
  • They stayed in LA together.
  • They ended the series as a couple.


  • 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 got back together in The Ghostest With the Mostest.
  • They ended the series as a couple.


Jessie logo
To view the Tessie gallery, click here.

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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