With the arrival of Jennifer Lindly into Capeside, came a cloak of mystery. Dawson found, what he considered, his new inspiration. Dawson made her the lead in his movie, casting Joey aside. Dawson followed her to a dance, he did everything in his power to show Jen that he was the one that she could be with, that he was the one who could make her happy. In the ruins, while taping the last scene of his movie, they shared their first kiss. The two became closer, until Jen revealed her reason for coming to Capeside: her parents caught her having sex in their bed. Dawson didn't understand how she could keep this a secret but the two eventually made up. Jen's ex-boyfriend, Billy, came to town to see Jen. Jen and Dawson broke up, Jen stating something along the lines of she needed time. In the meantime, Jen began to regret her decision when she noticed Dawson seeing Joey for the first time. Jen's grandfather died, sending her in a downward spiral. And the one thing she wanted was Dawson. Amiss Dawson and Joey's breakup, he began to spend more time with Jen. Jen showed him how to feel alive by doing normal things that teenagers do(among them skinny dipping, and tee-peeing someone's house.) And during all this, they found a new connection. After Jen was kicked out of Grams's house, she moved in with Dawson. But soon moved out when she found a better arrangement with the ever lonely Jack.

Jen has also been the one to comfort Dawson through the whole Pacey/Joey saga. She offered him nothing but understanding and compassion. She knew that he was in pain, and stood by her friend. And the only thing that she ever asks for in return is the same compassion and understanding that she gave, returned.