Jackson and Sookie meet through their employment at the Independence Inn. They constantly bicker over the quality of Jackson's produce, but are respectful of one another's respective culinary abilities. Sookie asks Jackson out and their first date unfortunately entails Jackson's cousin Rune tagging along (as Lorelai's date). However, the situation is soon rectified and the two start a sweet, beautiful romance.
After an argument about commitment, Jackson casually proposes to Sookie at the 2002 Bid On A Basket festival and she accepts. They marry in a beautiful outdoor ceremony at the Independence Inn. Most of Jackson & Sookie's marital fights are humourous and often spring from misunderstandings. Overall, Sookie and Jackson have one of the series' most stable romantic relationships.
Sookie's quest for quality in her food at times exasperates Jackson as he tries to meet her standards. They quite often bicker over whether the peaches are watery or the tomatoes are puny. It is not specified, but indicated that both Sookie and Jackson have worked together at the inn for years, perfecting their patented back-and-forth banter.
After a rude comment from Lorelai about the current state of Sookie's love life (which Lorelai immediately apologises for), Sookie asks Jackson out on a date. Despite interference from Jackson's cousin, Rune, the date ends well (Rune leaves to go bowling) and the two start a romance for the ages. Lorelai catches them being cute in the inn kitchen and they are later seen enjoying their first Firelight Festival together.
After dating a while, Jackson implies he wants to make a greater commitment to Sookie, who is oblivious to this at first, though later admits that she did get it, but was worried about risking their relationship, as it was going so well. Making up after a fight over this, Jackson skips a step and tells Sookie he thinks they should marry, to which Sookie says yes. The lovebirds start planning their wedding, and, with the exception of a detour into giant papier machê mushroom land (courtesy of Emily Gilmore), they have few disagreements about the big day and marry in a beautiful outdoor ceremony at the Independence Inn.
The newlyweds have their patented Sookie and Jackson squabbles, beginning with Sookie seemingly buying up everything Davy Crockett to be found at Kim's Antiques, in order to make her house more 'masculine'. More seriously, as the topic of kids come up, they disagree on the number of children and Sookie finds it difficult to communicate her feelings through her shock, leading to a fight which is quickly resolved. Jackson wanted 'four in four' – four kids in four years, but the two eventually end up having three children, with a few more years in between. The first is Davey, whom Sookie is pregnant with less than a year after she and Jackson marry. Davey is born in Autumn 2003.
- Sookie's pet name for Jackson is Mushroom Man.