Although not interested in each other during their first semester of their senior year, the two became attracted to one another as the year drew to a close. During this time, Damian was in a relationship with Liberty's friend Emma Nelson, but Damian and Liberty continued to flirt with each other behind her back anyway. The tension escalated between them until they hooked up at their senior prom, but were caught by Manny Santos and Toby Isaacs, whom they had told in secrecy. Toby, however, announced it to everyone, which caused Emma to end her relationship with Damian and friendship with Liberty. Liberty ends it with Damian when she realizes that they will not amount to anything.
In Rock This Town, Manny tries to hook up Manny and Damian by inviting him as Liberty's date to her 18th birthday party. However, the two find little to talk about it, and Liberty decides that he isn't the one for her, as she was still in love with J.T. Yorke. Manny, however, hooks up with him instead, as he had been attracted to her instead of Liberty.
Season 7In Don't Stop Believin', Liberty and Damian learn they have tied for the highest marks in class, so a vote will be conducted to determine who will be valedictorian. Liberty thinks that it would be a popularity contest and thinks she deserves to win because she has been working hard at Degrassi while Damian was at Lakehurst. After Damian begins being flirtatious toward Liberty. She asks him about the flirting. He denies it and says he's just being friendly, which upsets Liberty. After, Damian and Liberty are asked to make videos as to why they should be valedictorians. Liberty makes a rant about Damian to the surprise of Toby. When the videos are being shown to the school, Damian makes a very sincere, heartfelt video. Liberty feels bad about her own video, and to her luck the power goes out before her video is shown. Toby then gives Mr. Simpson the idea of allowing Liberty to do her speech on his video blog. In the end, Liberty ends up winning the election. Also, Damian admits he was flirting with her.
In We Built This City, Damian buys prom tickets for him and Emma from Liberty. The two flirt with one another by calling each other "Degrassi's smartest guy" and "sexy genius" respectively. While talking to Damian, Liberty gets a call and learns that Natasha Bedingfield will be playing at their prom, and she hugs Damian in her excitement. After their history exam, the two ask each other how they did, and Emma approaches them asking what is up since she had noticed it appears that they're keeping a secret. Liberty then announces to the senior class that Natasha Bedingfield is playing at their prom. Toby approaches Liberty and asks her to be his date, and Damian approaches her after Toby leaves, to which Liberty asks him what he expected since he is unavailable.While Liberty arrives at prom, Damian smiles at her and how great she looks. Later at prom, they run into each other and find out that they're both going to Banting University. Liberty asks Toby about what she should do about her attraction to Damian, and he gets angry at her and leaves, saying that "Following your heart sucks", since he had feelings for Liberty and thought they were on a date. Damian and Liberty sneak off during a song, which does not go unnoticed by Manny, who is furious into a pool closet. They proceed to kiss several times, and re-appear when everyone else is in the pool. Manny confronts Liberty about it while they are at the pool and tells her to keep quiet until after graduation to spare Emma's feelings. Damian later brags to Toby about Liberty, which causes him to yell at everyone about how they fooled around and Damian was bragging about it, and Emma is shocked and disgusted. She breaks up with Damian, not even sparing a glance at Liberty.
As of graduation, neither Emma or Manny will talk to Liberty. Liberty and Damian talk at graduation, and he tells her that Emma dumped him. Liberty tells him that they will amount to nothing, like both of his relationships with Emma and Manny. Liberty's friends forgive her when she begins to cry during her valedictorian speech, saying that six years of friendship is worth more than one mistake.
- They were both planning on going to Banting University, but only Liberty ends up going to Smithdale University instead.
- They both graduated with the Class of 2007.
- Damian was also romantically involved with Liberty's two friends: Emma and Manny.
- This friendship ended Damian and Emma's Relationship.