Trent Maddock was once a Harvard University classmate of Rebecca Bunch who is infatuated with her. He now resides in Los Angeles where he is the owner of a computer programming company. Trent has a penchant for turtleneck sweaters and an odd, off-putting personality. By happenstance he found himself reunited with Rebecca years later. Due to his proximity to West Covina, Rebecca's best friend Paula selected his online profile to be the basis of a fake relationship with his fellow alumni. They were at the time unaware how serendipitous the choice was; upon finding out Rebecca and Paula were creeped out but Trent's usefulness and willingness to help somewhat overcame their trepidation. Trent was as obsessed with her as she was with Josh Chan but took a more methodical approach to his romantic pursuit. When Rebecca was at a low point she slept with Trent and, unbeknownst to her at the time, took his virginity. Trent's first appearance was in the Season One episode "Josh and I Work on a Case!". He is portrayed by Paul Welsh.
Rebecca Bunch I have loved you since the moment that I saw you freshmen year in the cafeteria. You were eating a mac and cheese sandwich, remember? And then last week from out of the blue you friended me on Facebook and then some lady called me and said I was your boyfriend, I mean what are the odds? So weird, right?
–Trent, "Josh and I Go to Los Angeles!"
Trent Maddock was unexpectedly reunited with his Harvard classmate Rebecca Bunch when he got recruited to be her fake boyfriend. She was unaware he had a crush on her since thier time together at school and was more than willing to particpate in the facade. He carried out her scheme convincingly and used his participation to insinuate himself into Rebecca's life. Trent blackmailed her into letting him cook for her, give her massages, bathe her and also sleep at the foot of her bed. Although she had enough and kicked him out of her apartment he decided to try and win her affections through a grand gesture. At the time she was working on a huge lawsuit against the conglomerate known as Greater City water. To help her and get back into her good graces he hacked into the GCW computer servers and found incriminating evidence which could win Rerbeacc's case. During the trial's reccess he went to the courthouse and gave her the documents. Her grateful reaction to those files prompted Trent to ask if he could now sleep with her in the bed. She considered his request but sent him away before giving a definitive answer.
In 2016, Trent Maddock was surprised when he was friended on Facebook by his former Harvard crush Rebecca Bunch. On that same day he was then contacted by two West Covina residents Valencia Perez and Greg Serrano. They believed him to be Rebecca's boyfriend and curious about the situation he went to Perez's apartment to meet her, her boyfriend Josh and Greg. Before they could talk, Rebecca Bunch herself showed up unexpectedly oddly dressed in fly fishing gear. When she saw Trent she immediately kissed him much to his shock ("Josh and I Work on a Case!"). Trent responded enthusiastically until Rebecca pushed him off. She claimed he was her boyfriend and Trent decided to go along with the lie.
When Valencia asked them to explain a discrepancy with his online profile picture, Trent covered for Rebecca again explaining he mislabeled the photo. After kissing Rebecca once more he left and told her he'd meet up with her later. Trent later went to Rebecca's apartment, snuck in through the patio door and waited for her. When she finally showed up Rebecca was startled to see him and asked if he was going to kill her. Trent put her at ease by explaining he'd been in love with her since Harvard when in freshmen year he saw her eat a Mac and cheese sandwich. Rebecca thanked him for lying for her but told him nothing romantic was going to happen between them. Trent responded by threatening to tell her friends the truth unless Rebecca had dinner with him.
Rebecca reluctantly agreed and even allowed Trent to draw her a bath and massage her feet. He was there the next night as well and again Rebecca insisted he leave as she had a long day. Trent piqued her interest when he mentioned he prepared homemade tagliatelle. He continued to win her over with a shoulder massage and she begrudgingly allowed to stay. During dinner, Rebecca told Trent that while she believed she had a solid case against Greater City Water she didn't have any hard evidence that could definitively prove their guilt. Afterwards, Rebecca rewarded his efforts by allowing him to sleep at the foot of her bed. However, in the morning Rebecca kicked Trent out of her apartment. She closed the door on him as he tried to read her a love letter he wrote to her when they were both in college.
In order to further please Rebecca Trent decided to hack into Greater City Water's servers and found the evidence Rebecca was looking for. During the recess of the trial, Trent went to present his findings to Rebecca. She at first dismissed him believing he was there to bring her more food. He quickly got her attention when he showed her the incriminating emails he discovered that detailed Greater City Water's guilt. At the time the trial wasn't going well as her star witness's credibility had been destroyed by her opposing counsel Audra Levine. She was so incredibly grateful for Trent's efforts that she seriously considered his request to sleep in bed with her. Instead of answering she sent Trent away as she wrestled with whether or not to use the illegally obtained evidence ("Josh and I Go to Los Angeles!").
Months after the trial, Trent came up with a plan to win Rebecca's heart. The first step was becoming friends with Josh Chan, White Josh and Hector. He invited them to watch the game at Home Base and paid for the steep cover charge Kevin instituted. The night went poorly as they were put off by his odd personality. After they left a saleswoman Trent met earlier encouraged him to pursue Rebecca directly. Trent went to Rebecca's new home where he wound up lifting debris that had trapped her friend Paula in the bathroom. He later apologized to Rebecca for trying to force himself into her life. Rebecca was still upset about a fight she had with Paula and decided to sleep with Trent. Afterwards, she was surprised not only by how good the sex was but also when Trent thanked her for taking his virginity ("Who Needs Josh When You Have a Girl Group?").
Months later, Rebecca got engaged to Josh Chan and a website was created to make the announcement official. This was noticed by Trent who declared the marriage would happen over his dead body ("Is Josh Free in Two Weeks?"). Trent decided to investigate Rebecca's time at Harvard to find something that could drive a wedge between her and Josh. He travelled to Massachusetts where he bribed a state official to give him Rebbeca's file. Trent found what he was looking for and flew back to California arriving on the day of the wedding. He went to Rebecca's house where he found Josh about to leave for the ceremony and handed him the file. When Josh asked if it had something to do with Harvard and Robert Trent teased it as a possibility before leaving with a smile ("Can Josh Take A Leap Of Faith?").