Love Triangle History
Toby and Liberty had been good friends for years, and he had developed an unrequited crush on her after the death of their friend and Liberty's ex-boyfriend, J.T. Yorke. In their senior year, Liberty still did not return Toby's feelings, but developed an attraction to Emma's boyfriend, Damian, near the end of the year. Toby asked Liberty to their prom, which she accepted, but at prom, she ended up hooking up with Damian. Damian and Liberty confessed what they did to Toby, who exposed their affair to the rest of their friends. Liberty reconciled with everyone after apologizing at graduation and ending her affair with Damian.
In We Built This City, Toby asks Liberty to prom as his date, and she accepts, though makes it clear that they're only going as friends. Manny, Liberty, and Emma have an all girls + Toby hug before the prom when they realize they're all going their separate ways soon. When Natasha Bedingfield toasts to Liberty, Toby gives her a side hug. Later, while dancing with Toby, Liberty asks Toby what to do about her feelings for Damian, and Toby is angry that she was thinking of Damian while on a date with him, revealing she still only thinks of Toby as friends, even though he felt the prom date meant more. Later, Liberty confesses to Toby that she followed her heart with Damian, but when Damian starts bragging about their hook-up to Toby, Toby reveals to everyone that they hooked up. Manny, Liberty, and Toby do not forgive Liberty until she breaks down crying in her graduation speech about how special friends are for the journey together. They all reconcile, and place a graduation hat by J.T.'s memorial at the schools.
- Toby has had an unrequited crush on Liberty since the sixth season.
- Damian was in a relationship with Emma Nelson when he and Liberty hooked up.
- Start: We Built This City (724)
- Ended: We Built This City (724)
- Reason: Liberty chose her friends over a possible romance with Damian, though she still did not return Toby's feelings for her.