Skyler is Teddy's friend. She dated PJ Duncan for a length of time before she moved to New York. She later gets back together with PJ Duncan in Good Luck Jessie: NYC Christmas. She is portrayed by Samantha Boscarino.


Skyler isn't the smartest person in the world. She doesn't catch on very fast and gets confused easily. But she can be very sweet and kind. Just like PJ, she is also childish. As shown in their relationship.

Personal life

Skyler was introduced in "Girl Bites Dog" as the girl Spencer was cheating on Teddy with. Skyler later became friends with Teddy in "Teddy's Broken Heart Club Band". Skyler starts dating PJ in the episode "Battle of the Bands" and continue dating till she moves away in "PJ in the City". Skyler returns in the Season 4 episode "Good Luck Jessie: NYC Christmas" where she and PJ admit they are still crazy about each other and get back together. She is graduating high school and going to Denver University.


PJ Duncan

Main article: Pyler

PJ and Skyler meet in the episode "Battle of the Bands" and they have an instant attraction. They become a couple later in the episode. PJ and Skyler are both portrayed as very flighty and not very bright. In the episode "Teddy's Bear", PJ and Skyler celebrate there one week anniversary. Skyler wrote a poem for PJ and he got Skyler a necklace with a piece of the Churro which was the first snack they ever shared together. PJ also tells Skyler's ex "Brock" to back off. In the episode "Meet the Parents" Skyler and PJ go on their first real date. In "Monkey Business" PJ thinks Skyler's dad was watching him, but later in the episode PJ finds out that he was just hired to pretend to be her father. PJ makes it clear he is the one for Skyler.  In "PJ in the City", she has to say goodbye to PJ because her dad got transferred to New York. They both are devastated and don't want to say goodbye. PJ goes to New York to be with Skyler. Eventually Bob convinced PJ if him and Skyler are truly in love they will find a way to eventually be together. They break up but they both tell each other that it isn't a goodbye. It's just a see ya later. Skyler returns in the Season 4 episode "Good Luck Jessie: NYC Christmas" where her and PJ admit they are still crazy about each other and get back together. Skyler appears in the finale Good Bye Charlie as PJ's Girlfriend. PJ and Skyler end the series together as Boyfriend and Girlfriend.

Teddy Duncan

Teddy and Skyler are friends. They performed together with PJ and The Vibe in the Battle of the Bands. They were both dating Spencer at the same time and they struck up a friendship from the momentary hatred towards Spencer Walsh.

Ivy Wentz

Skyler became Ivy's friend in Teddy's Broken Heart Club Band.


Skyler's past boyfriend, Brock, is captain of the wrestling team.

Spencer Walsh

Skyler dated Spencer for an unknown amount of time. They broke up after Skyler found out he was cheating on her with Teddy Duncan.


  • "It must be nice for your girlfriend to have a boyfriend with such great hair."
  • "Oh, no problem. PJ has been keeping me company."
  • "That's right. PJ's my dude."
  • "Wow, it's so fun going out with a smart guy."
  • "The hard part was getting it to rhyme, so I didn't."
  • "Aww, that makes me so happy."
  • "It's just that we've been seeing each other for three weeks and we haven't even gone out on our first date yet."
  • "Like sometimes their name. Or if the relationship is meant to be."
  • "Yeah, an awesome first date sets the tone for the entire relationship. I saw it on a cover of a magazine."
  • "No, I'm not a big reader."
  • "What first date? No one's asked me out yet. Hint, Hint."
  • "Puked in the picnic basket is an expression? I don't think that's going to catch on."
  • "Yeah, that would have been awful. Talk about puke in the picnic basket."
  • "I tried it once with a pineapple. Not as fun."
  • "I love learning new things about you."
  • "Oh, um, I better go. But first I want a picture of you and me."
  • "Well, I better go....Goodbye PJ."
  • "Yeah, I'm fine. It's just that..I'm fine."
  • "Dear PJ, I have something to tell you so I'm writing this note. But since your not a big reader. I taped it for you instead. There's a boombox on the bench. Hit play. So this is kind of hard. I have to tell you that.. I'm sorry. I can't go on. Just go back to the note.  I've got some really bad news. My dad has been transferred to New York City which means I'm moving there. I wanted to tell you but it made me so sad to say goodbye I just couldn't. I'll miss you forever. Oh, by the way. This is Skyler. Now press play again."
  • "Aw, PJ. Can you believe he came all this way for me? It's so romantic."
  • "Yeah, he wants to make money to get his own apartment. He's working on Wall Street."
  • "Well, Under Wall Street."
  • "So, even though you won't find another guy who's as crazy about you as I am. I set you free." Skyler tells PJ "And even though you'll never find a girl who's crazier than I am. About you. Your free too."
  • "See, this is exactly why I didn't want to say goodbye to you."
  • "Well, It was good seeing you."
  • "He helped me realize that I'm still crazy about you to."
  • "I mean you'll be in Denver and I'll be off to college."
  • "Denver University."


The image gallery for Skyler.


  • Although Skyler isn't really smart, she seems to be able to play instruments like the piano, guitar, and vocal exercises.
  • She and her new boyfriend PJ claim that they never get the look Teddy gets when she has an idea.
  • She likes the Gurgles, just like PJ when he introduced it to her.
  • She leaves the show in season 2, likely because her portrayer, Samantha Boscarino, was a main cast member on Nickelodeon's new show, How to Rock.  


Season 1

​Season 2

Season 4