Luke and Jess had one of the most complex relationships in Gilmore Girls. While Lorelai and Rory are the protagonists with a bond that’s envied and dissected, it’s Jess and Luke’s relationship that rivaled theirs. The two men had their battles over the years but they also had some tender moments.
Luke wasn’t Jess’s father but he was the closest thing to a father figure that Jess could have had. Luke pushed Jess to go to school, to work hard, and to make something of himself. Jess had other plans that didn't involve school, but he eventually came around to respect and even love his Uncle Luke. Even in their darkest moments, there’s nothing Luke or Jess wouldn’t have done for each other.
'Swan Song' (Season 3, Episode 14)
Jess was embarrassed when he showed up at Emily Gilmore’s house late for dinner with a black eye. Rory begged Jess to tell her what happened but he refused. That night, he told Luke the truth about his eye: a swan attacked him. Luke laughed at first but eventually agreed to track down the swan together.
The two went to the lake and sat in a small boat until the swan made its presence known, and it quickly became one of the silliest moments between the two. The fact that Luke took the time to look for the swan that attacked his nephew was humorous yet sweet.
'Last Week Fights, This Week Tights' (Season 4, Episode 21)
When Jess was in town for his mom’s wedding, he and Luke reconnected. Luke had a realization not long before Jess’s arrival that he had feelings for Lorelai, and thanks to a self-help book, Luke took the advice and acted on his feelings.
He told Jess what he learned from the book and ended up giving it to him as a gift to work on himself. Jess acted like the book was a joke but he was later seen reading it. If that wasn’t endearing, the fact that Luke defended Jess when Lorelai mocked the self-help book in Jess’s bag sure was.
'A Tale Of Poes And Fire' (Season 3, Episode 17)
Jess was brooding and aloof but people can’t say he wasn’t a hard worker. As much as he hated working at Luke’s Diner, he worked hard and showed up when he was needed and deserved a second chance.
Outside of Luke’s, he also got a part-time job at Walmart. And apparently, he worked just as hard at Walmart as he did at Luke's because he was awarded the employee of the month award. Adorably, Luke showed up at Walmart to congratulate Jess on his accomplishment.
'Teach Me Tonight' (Season 2, Episode 19)
Luke was horrified when Lorelai showed up at the diner looking for Jess after Rory and he were in a car accident. She and Luke were screaming at each other because of the fear Lorelai was feeling over her daughter being in a hospital.
When Luke eventually found Jess, he approached him softly. He knew Jess was scared and felt horrible. Jess told Luke that he made sure Rory was okay before leaving the hospital. With a knowing look, Luke understood and sat with him in silence.
'The Ins And Outs Of Inns' (Season 2, Episode 8)
In season 2, Jess walks into the diner and judges Luke for his shotty job at fixing the toaster. Luke had to resort to using a smaller toaster in the meantime. But by the end of the episode, Luke's toaster was magically fixed.
Luke asked "bad boy" Jess if he was the one that fixed it but Jess ignored him and went to school. Their banter before leaving was proof that Jess had a soft spot for Luke and wanted to help him without the credit.
'Luke Can See Her Face' (Season 4, Episode 20)
It's not often that Luke and Jess were calm enough to have a heart to heart but Jess grew a lot as a young man in season 4.
With his mother's wedding around the corner, Jess told Luke he was uncomfortable being back in Stars Hollow because he told Rory he loved her a few months prior. Luke was shocked by his admission and gave him some advice from the self-help book he was reading.
'Lost And Found' (Season 2, Episode 15)
When Jess first arrived in Stars Hollow, he and Luke were still getting to know each other and getting used to living together. Luke stormed into his apartment above the diner to find Jess sleeping with music blaring over the stereo. He couldn’t help but yell about the noise and the mess that his home now consisted of.
However, as Luke was leaving, Jess said that he couldn’t sleep without the music on. Instead of ignoring Jess, Luke put the music back on for him. It was a subtle act of kindness but it proved that Luke had a soft spot for his nephew.
'Last Week Fights, This Week Tights' (Season 4, Episode 21)
On the day of Liz and TJ's wedding, Luke and Jess were getting ready in Luke's apartment with TJ. TJ came out of the bathroom and told Luke he had to use his deodorant.
Luke responded calmly but fans knew that Luke was dying inside at the thought of TJ using the same deodorant. Jess knew exactly what Luke was feeling and without many words, he dropped the deodorant in the trash.
'A Family Matter' (Season 4, Episode 12)
At the start of season 4, Rory and Lorelai walked by Luke’s and found Jess sleeping in his car. Both Lorelai and Rory didn’t care for Jess at this moment but they didn’t want him sleeping in the car when it was freezing outside. Lorelai told Luke that as angry as everyone was at Jess, he didn’t deserve to freeze in his car.
As Lorelai left, Luke told Jess that he could go inside if he wanted to because he was going to Nicole’s for the night. He waited a few minutes to make sure Jess made it inside before leaving. His actions were what any father would do for their child and it spoke volumes about his character.
'Last Week Fights, This Week Tights' (Season 4, Episode 21)
After Liz and TJ's wedding ended, Jess was gearing up to leave Stars Hollow but waited around for Luke to say goodbye. Suddenly, Jess told Luke that he wanted to pay him back for everything he's done for him over the years.
"I appreciate it...everything -- the money, living here," Jess said. Luke knew where Jess was coming from and appreciated his kind words. They embraced and further cemented their sweet bond.