As far as romance goes, the two once tried, or the rest of their friends tried to fix the two of them up at a school dance. Dawson punched Jack for making a move on Joey and Jack and Jen left together.

Over the next several incidences in Jack's life, he turned to Jen, because he knew that out of all their mutual acquaintances, Jen was the one who could listen the best without passing harsh judgment onto him. Jack also helped Jen when she needed it. Jen moved in with Jack after her Grams kicked her out. The two became closer, talking about things like suicide and Jack ultimately pushed Jen to reconcile with her Grams. Jen told her grandmother that she didn't want to be alone anymore and neither did Jack, and he moved in with the two.

Jack and Jen soon found their way into a groove, where they knew systematically what the other wanted, they proved this over breakfast. Jack and Jen saw each other through numerous other things in the beginning of school (i.e. Jack went with Jen to cheerleader tryouts, Jen supported Jack during his football endeavor, and Jen told Jack that he would soon have an amazing love life). Then came the time when Jack saw that his sister needed him. Jack approached Jen and Grams, thanked them for their allowing him to be a part of their family and told them that Andie needed him, to which Jen replied, "Go home, Jack". The two have remained friends, although we haven't exactly seen it.

If I ever had a gay best friend, I would want a Jack. Loyal, trusting, and cute as can be. Jen would be my choice as a friend for a girl. Together these two have become two of the most popular on the show. They are the friends everyone wants and are the friends everyone loves to watch. Everyone loves the two BEST FRIENDS.