Thomas is the only child of Jim and Carolynn, who are both at home work-a-holics and therefore chose to homeschool him for their convenience. Since he doesn't spend much time with either of his parents nor does he have siblings, Thomas latched onto his dog, Sammie, who a mutt and became his best friend. Shortly before meeting Ashley, however, Sammie passed away, and left Thomas so heartbroken that he still couldn't bear to put away Sammie's bed and toys.
Thomas met Ashley on November 30, 2008, at a public bus stop. He told her how his dog had recently died, offered her a cigarette, yet neither of them smoked and ended up throwing the pack away, then he asked her to skip school with him, but she was busy waiting for Ben Boykewich, so she declined.
He saw her again on December 2, 2008, and wondered why her parents weren't more protective of her. He didn't believe that they didn't know she had left the house without telling anyone, so he called her house and discovered that Ashley was telling the truth when Anne Juergens said she'd tell Ashley he called. They then discussed Ashley's invisibility, how she'd gotten a job as a cocktail waitress even though she was underage, and even though she lied to him about his age he could tell she was lying. He later admitted that he didn't go to Grant High as he initially said, but he was instead homeschooled and his parents were not good teachers, then he eventually asked if he could come over to Ashley's house later that night and she agreed. When he arrived at her house, he brought a bottle of wine for Anne and George Juergens and seemed to be impressed with George's garage apartment. They discussed conspiracy theories, then settled into a routine of her making him dinner and post-dinner conversation. Finally, Ashley decided that she wanted to visit his house and his parents.
On January 10, 2009, Ashley came over to Thomas's house for the first time and met his parents.
By February 5, 2009, Thomas and Ashley had broken up. Ashley had broken off their relationship at the bus stop by saying that she didn't want to see anybody at that time. She later told her mother that she had broke up with Thomas because she wanted passion in a relationship, instead of one that was just comfortable. According to The Secret Diary of Ashley Juergens, Ashley did not think Thomas was too broken up about the breakup and she heard that he eventually found "another bus stop."