|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!").