Sydney Ashdown  (Sydney Thomas), is a Sophomore "solo-pianist-singer” and a high school, popular rich girl. She has a flair for fashion and comes prepared to talk to her best friend Savannah Swanson during class while any of the teachers are giving a lesson. She is 15, then turns 16, during the school year. Sydney is a bit of a bad girl, prone to sarcastic remarks, talking through the entire class on the phone and face to face with friends, even telling the teacher “why are you teaching during my conversation” when confronted by Mrs. Hialeah. Late in season one; Sydney develops a crush on Landon who is a college psychology student teaching and observing at her school, while in a relationship with Jake. 

Sydney often goes by the nickname Syd, especially by the students she is surrounded by. She and her best friend Savannah are always hanging around guys or sipping coffee at a local café, during, before, and after school. 

Sydney, is instrumental, literally in the first year school madrigal show choir making it to finals as a pianist and vocalist.

Sydney takes the advice of rival student Londyn Downey, to get Keratin treatments at a high end salon when her close friend Teagan Janney, meets up with her.  Teagan mentions she is surprised the two aren’t meeting up with Savannah and Thea at Starskie’s, Sydney states “No…No Savannah needs time to reflect. She’s thinking about Shane non-stop. I know she’s my best friend, but she needs some time alone.” This is the only moment in the series where Sydney is purposely staying away from her bestie Savannah.

A solo song and piano East Valley Academy Show Choir Audition scene - Sydney Thomas as Sydney Ashdown - Up on High Ground TV

Like Savannah she lives with her father in a four bedroom mini-mansion in a cul-de-sac on private property. Jake mentions that Sydney has a sister named Astoria, which he sang alongside in summer camp, and she has a cousin named Merdes, in DeKalb Illinois that he went to State Show choir with. Jake reiterates to her that it was no coincidental connection that he is meant to be with Sydney.

Jake, Sydney's current boyfriend, indicates the two have been going out for a while, reminding her it’s been 8 months when she mistakenly said it was 6 months in the episode “Gone, But not Forgotten”, Jake is oblivious to Sydney’s liking college student Landon Lofton. Jake continues to support her, he often posts YouTube videos of the two together singing. Sydney mentions Jake’s parents offered her a job as a solo-artist singer under a small record label in Seattle upon graduation.

Jake makes a heartfelt move to solidify his relationship with Sydney by surprising her with a promise ring. Sydney is very happy by the sweet gesture and accepts the ring with a kiss for Jake. Later, when talking with Savannah, she reveals that she is torn between having feelings for Jake and Landon.  Savannah reminds her she was intending to break up with Jake and how the promise ring complicates things.

 Sydney is very close to her Grandfather who has Alzheimer’s, in “Friends, Family, and Freeloaders, Part 2”, she is prepared for a good read at the East Valley Academy library however she is unexpectedly confronted by an embarrassing moment when Grandpa Ashdown is at her school thinking it is the public library.  Upon an obvious moment of ridicule from a few classmates, her grandfather makes the situation worse by falling into a small bookshelf-cart.

Sydney surprised as ever to see her best friend Savannah finally make peace with her class rival on stage, is moved by the moment, and takes a risk herself with Landon. With the ongoing feud now mutually over between Erin and Savannah, Thea tries to overshadow it by bringing Erin in on what she thinks is inside info on Sydney and Landon's age difference relationship.

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