Gilmore Girls: Sookie And Jackson’s Relationship Timeline, Season By Season

Between Rory’s love for Dean, Jess and Logan and the different relationships that Lorelai commits to on Gilmore Girls, there are several love stories with a lot of screen time. But no matter how much fans love following those romances, Sookie and Jackson also have a great, solid, and endearing love story that stands the test of time.

From their awkward yet adorable first date in season 1 to getting engaged, married, having kids, and balancing work and family time, Jackson and Sookie have an incredible long-term relationship that changes in each season of Gilmore Girls.

8 Season 1: The Sweet, Nervous, Early Days Of Dating

When fans look back on the best things about Gilmore Girls season 1, Sookie and Jackson’s first date is definitely up there. After knowing each other for a long time and having nervous, flirty exchanges about fruit and vegetables, Sookie asks Jackson out on a date and they go out with Lorelai and Jackson’s awful cousin Rune in “Double Date.”

Season 1 is all about the sweet, charming, and sometimes nerve-wracking early days of Sookie and Jackson’s relationship. It’s great to see the show focus more on Sookie’s love life instead of the drama surrounding Lorelai and Max’s love story. Fans don’t know about Sookie’s romantic past, but it seems like Jackson is a better, more mature and intelligent partner for her than anyone else could be.

7 Season 2: Engaged, Excited, And Married

Sookie and Jackson’s relationship kicks up another level in season 2 as they get engaged while having a romantic picnic in the episode “A-Tisket, A-Tasket” and get married in the season finale “I Can’t Get Started.”

It’s sweet and exciting that the couple has such a short engagement, as they can’t wait to start their lives together, and they also figure out that they might be a bit scared of the future but they want to face it together. Although Jackson is nervous to get married at first and he says that he would be fine living together, he does propose and fans are glad to see Sookie so happy.

6 Season 3: Starting A Family

Although the Gilmore Girls parents make mistakes, it’s heartwarming to see Sookie and Jackson so thrilled to be expecting their first child in season 3.

This season is all about Sookie’s pregnancy experience, along with her concerns that she might not be the best parent that she wants to be. Viewers feel badly that Sookie is so nervous about this, as she is intelligent, funny, compassionate, and caring, all things that make parenthood at least a little bit easier. It feels satisfying to see Sookie in a happy relationship after all that she has done to help Lorelai and Rory.

5 Season 4: Adjusting To Parenthood And Supporting Career Dreams

Gilmore Girls fans appreciate how happy Sookie and Jackson are together, but viewers wonder why Jackson tells Sookie that he wants four kids in four years and why he doesn’t seem to hear Sookie tell him that it’s too intense for her.

In season 4, Sookie and Jackson adjust to being parents to their baby Davey and Sookie and Lorelai also work on opening the Dragonfly Inn. While viewers wonder why the couple doesn’t have more meaningful conversations about how many children they want, they do stay together and seem to bring each other joy.

4 Season 5: A Second Pregnancy And Jackson’s Political Campaign

Season 5 of Gilmore Girls has funny, sad scenes and Sookie and Jackson’s love story gets a bit more dramatic as the couple deals with another pregnancy and some career changes.

As Sookie learns that she’s having a second baby, and she tells Norman Mailer about her pregnancy at the Dragonfly Inn in a hilarious scene, Jackson runs against Taylor for town selectman. As Sookie shares that being pregnant is tough for her since has her two babies so close together, Jackson doesn’t want to run Stars Hollow. Sookie is there for Jackson the whole time and while fans know that they don’t have the same idea of how many kids they want to have, they do support each other.

3 Season 6: A Happy Relationship While Sookie Focuses On Lorelai

As Sookie and Jackson adjust to having two children in season 6, they don’t fight much and seem to be doing well at this point in the show.

Sookie and Jackson don’t experience dramatic changes in their long-term relationship the way that Luke and Lorelai do. In season 6, Sookie shifts her focus to Lorelai and Luke’s wedding, which Sookie really hopes will happen soon. Fans love what a great friend Sookie is and can tell that Lorelai and Luke most likely won’t tie the knot this season.

2 Season 7: A Third Pregnancy That Fans Feel Strongly About

When Gilmore Girls fans talk about season 7, they feel strongly about Sookie learning that she’s pregnant with her third baby. Sookie asked Jackson to get a vasectomy and when she’s shocked to be expecting another child, Jackson says that he didn’t get the procedure.

Although fans love this couple, it’s impossible to agree with Jackson’s decision here as he needed to talk to his partner about this situation, and this is a tough and strange storyline.

1 A Year In The Life: Sookie’s Living Her Dream

Fans want to see Jackson and Sookie doing well in A Year In The Life, and while Jackson is in the revival even more briefly than Sookie, it seems that they’re still happily married and raising their family while thriving in their careers.

In the “Spring” episode, Jackson has a stand selling his produce at the Stars Hollow International Spring Food Festival, and he says that Sookie is busy so she couldn’t be there. Jackson seems proud of Sookie for working with Dan Barber, and if there is ever a season 2 of the revival, it seems likely that the couple would be just as content in those new episodes.

About The Author

Aya Tsintziras
(1738 Articles Published)

Aya Tsintziras is a freelance writer who writes about pop culture and TV. She has a Political Science degree from the University of Toronto and a Masters of Journalism from Ryerson University. She loves coffee, reading, working out, and watching TV. She lives in Toronto with her husband.

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