|Greg was tending bar at Home Base when Rebecca Bunch walked in. She had just moved to West Covina from New York and was at the bar to meet a mutual acquaintance Josh Chan. She accepted his invitation to go with him to a house party Josh was to attend. After a brief nap on his couch, Greg picked Rebecca up at her place and complimented her on her appearance. At the party Greg was put off by Rebecca's obsession with Josh. To avoid the issue she started making out with him. She had an emotional breakdown when Greg received a text message from Josh revealing he had a girlfriend. Greg decided to take her home and on thier way out they bumped into Rebecca's co-worker Paula Proctor. The two walked off to have a private conversation leaving a confused Greg behind ("Josh Just Happens to Live Here!").
A week later Greg was at the grocery store with Hector and "White" Josh when he bumped into Rebecca. He wanted to talk about what happened at the party but Rebecca was in a rush to leave. They were interrupted by Hector and White Josh whom Greg introduced to Rebecca. An awkward scene ensued when Josh Chan and Valencia showed up too. Surprisingly, Rebecca and Valencia became friends and Greg joined them alongside Josh to a night club. Things went south when Rebecca got drunk, kissed Valencia and revealed she and Josh used to date when they were teens. A furious Valencia forbade Josh from ever seeing Rebecca again and left the club. Greg tried to comfort Rebecca but she rejected him and left ("Josh's Girlfriend is Really Cool!").
Greg is bartending at Home Base when Rebecca walks in and flaunts her cleavage before inviting him to a housewarming party. Greg refuses pointing out the last few times they were together didn't end well. She asks him to reconsider but her efforts stops when she spots Josh. The night of the party Greg is working at Home Base but it's deserted as his regular gamblers anonymous customers are no shows. He headed over to Rebecca's party found all the gamblers at her place. Nevertheless, he finds Rebecca and congratulates her for throwing a great bash. He later gets drunk on a bottle of Jack Daniels and slow dances with a giant fish. After the party ends, Rebecca allows him to take the bottle and calls a ride sharing service to take him home ("I Hope Josh Comes to My Party!")
A week later at Home Base, Chris and Josh encouraged Greg to ask Rebecca out when she showed up at the bar declaring she was making healthier life choices (♫ Settle For Me ♫). When she finally got back to him, Greg took her to the local taco festival. After some awkward small talk the two began enjoying themselves until they went to a guacamole contest. They had a brief argument about her commitment to being a vegan which Greg apologized for. She went to the restroom but never retuned and sent him a text saying she was sick. He was furious when went to her apartment that evening and saw a guy leaving her place. He demanded an explanation but all Rebecca could say was that he should see now how messed up she is and that he shouldn't waste time on her. Greg replied that all he could see was how this night could have turned out and left ("I'm Going on a Date with Josh's Friend!")
Several days later, Greg ran into Rebecca at Cup of boba. She was there with Josh and he accused them both of being bad people. To prove him wrong Rebecca got Darryl temporary full custody of his daughter Madison. Greg wasn't impressed with her efforts (♫ I'm a Good Person ♫) and rejected her offer to sleep with him to make up for the bad date they had. This only inspired her to do something more crazy to prove she was a good person. When this backfired, Greg observed her settling Darryl's custody dispute with his ex-wife amicably. He talked to Rebecca afterwards and she sincerely apologized for what happened. She had done all this to prove not only to him but to herself that she was a good person. Greg replied that he was still unsure about her but conceded she did a good thing for Darryl ("Josh and I Are Good People!").
After years of saving, Greg finally got enough money to move out of his father's house and attend business school. At Home Base Greg told Rebecca his plans and she invited him out for a celebratory drink later. Greg had prepared a big speech for his boss Kevin before he quit but it was unsatisfyingly anti-climatic when he delivered it. Greg went home to tell his dad he was moving out but before he could his father passed out. Greg had him taken to the hospital and was told he needed several very expensive procedures. He used his savings to pay for the medical bills and stayed a bit with his father. Later he went to Rebecca's place for the drink she offered earlier. Together they watched the Westminster Dog show which was an annual tradition Rebecca and her mother had on Thanksgiving ("My First Thanksgiving With Josh!").
Greg and the rest of the crew were asked by Josh Chan to help him build a dining room table. This was a housewarming gift for Valencia whom he had just moved in with. They were all at Greg's father's house assembling the table since Chan intended this to be a surprise. Both Greg and White Josh were unsure this was a good idea since Valencia usually had to personally approve anything Chan did. As they struggled to accomplish the task Greg and Wilson tried to subtly suggest to Chan that he break up with Valencia. However, Hector derailed the conversation with a monologue about tandem parking. When they finished putting the table together they presented it to Valencia who, as Greg and Wilson predicted, didn't care for it ("I'm So Happy That Josh Is So Happy!").
In December, Greg runs into Heather Davis working at the mall while he was shopping for Christmas presents. He had briefly met her months ago at Rebecca's house warming party. Upon hearing him complain about the bountiful Christmas dinner at his rich step family's house he was forced to go to she convinced him to take her with him. He warns her about how awful they are but when they get there it turns out he's the one with the bad attitude. Although she only came for the food and because she thought Greg was cute she points out the obvious chip he has on his shoulder regarding his mother leaving. Greg realizes she is right and has been holding a grudge for years without considering his mother's side of the story. Afterwards, Greg thanks Heather for helping to fix his relationship with his mother. Heather unexpectedly pulled him into a kiss which he reciprocated in kind ("My Mom, Greg's Mom and Josh's Sweet Dance Moves!").
Sometime later, Greg joined the crew and Valencia at the movie theater to watch a film. Afterwards, Greg was convinced by the others to join them for a beach trip. Rebecca Bunch also ended up invited to the outing and provided the transportation. Greg annoyed Josh when it turned out he invited his girlfriend Heather and Rebecca herself seemed taken aback that they were dating. The beach trip turned awkward when Rebecca performed a pole dance which led to her admitting she hooked up with Greg not long after she moved to town. This created tension between Greg and Josh and led to another revelation that Rebecca lied about her reason for moving to West Covina. Unable to process yet another excuse she had, Greg and Heather left the bus after it reached it's destination ("I'm Going to the Beach with Josh and His Friends!").
Greg gets spooked when Heather wants them to become serious and he suggests they go on a break. While at work, White Josh and Hector criticize him for his commitment phobia. They all accepted an invitation to watch a PPV fights with Darryl at his place. Hoewever, they got bored with the matches and were about to leave when Darryl suggested he could liven up the festivities. A group of women to show up and one of them turned out to be a former classmate of Greg's named Ashley Pratt. Greg had been in love with her since kindergarten and they wound up hitting it off. Ashley told Greg he was someone she could see herself getting serious about. Greg's commitment fear kicked in and he realized his friends were right. He found Heather the next day to apologize to her and although she made him squirm for a bit she eventually took him back ("I'm Back at Camp with Josh!").
Greg went over to Rebecca's apartment to get a hard drive Heather was borrowing from her neighbor. Greg had been avoiding Rebecca but went anyway which resulted in awkward small talk about her place's new decor and his relationship with Heather. That night Greg was leaving Heather's apartment and walked by Rebecca's place and noticed her glass patio door had been smashed in. Concerned he went inside and found Rebecca depressed and happy to see him. He eagerly offered to help stay and clean up the mess but became angry with himself after learning he was in the aftermath of one of Rebecca's schemes to win Josh. He ignored Rebecca's pleas to stay and left unwilling to to be second choice again ("That Text Was Not Meant for Josh!").
Later, Greg got Heather an interview with his boss Kevin who hired her immediately. Heather tuned the bars television to a local trial in L.A. involving Rebecca and her firm which annoyed Greg. Heather noticed this and his awe when Rebecca gave an emotional closing argument. Realizing her boyfriend was in love with Rebecca, Heather broke up with him (♫ Don't Settle For Me ♫). Greg took Heather's advice to confess his feelings but when he arrived in L.A. he found Rebecca and Josh kissing each other ("Josh and I Go to Los Angeles!"). Days later at Home Base, Chris warned Greg that things between him and Heather might be awkward now. He confronted Heather who admitted she was heartbroken about their break up and promised to give her space ("Josh is Going to Hawaii!").
One day Greg received a text from Darryl who was concerned about Rebecca's whereabouts. He showed up at Rebecca's apartment where he found Josh, Paula and Darryl trying to figure out where she was. Greg pretended not to care and assumed Rebbeca's disappearance was yet another of her whims. However, Greg secretly helped with the search by checking with local hospitals and morgues to find out if someone matching Rebecca's description was there. After some snooping Paula found out Rebbecca had gotten an email from her old firm offering her a job. While the others were in mourning about Rebecca possibly leaving Greg maintained a facade of indifference. This changed when Rebecca returned and Greg was surprised when she sincerely thanked him for caring ("Josh Has No Idea Where I Am!").
Greg is at a bar studying for his business class when Rebecca walks in. He invited her to join him but she declines unwilling to be around him when he is drunk. At school, Greg is angered when his teacher gives him a bad grade on a test and criticizes his lackadaisical efforts (♫ I Could If I Wanted To ♫). He goes to Country Market to buy some coffee and runs into a store clerk named Marty whom he met briefly. After learning Marty is in a love triangle Greg decides to help him out. However, Greg is unsuccessful and it makes him realize he needs to give up on Rebecca. He tells her this the next time he sees her at the bar only for her to abruptly leave and then return. Greg is shocked when she kisses him and declares this time he isn't second choice
("Josh's Sister is Getting Married!").