- „As much as I love those people in the next room, I'm happy with you. And no one else gets to weigh in on that”
Dawson met the girl next door at some point when they were kids, but they reacquaint when Jen moves to the Creek. Instantly attracted to each other, Dawson pursues a romance and they eventually get together, but break up due to Jen's tough upbringing and her feeling lost in her life.
The two form a solid friendship following Dawson's break-up with Joey, but when Dawson's father passes away, Jen manages to find a way to reach Dawson and be there for him, and at a getaway to a film festival, they reunite.
Jen and Dawson re-meet when they're 15, Dawson's greeting indicating that he knows Jen from when they were younger or has at least seen her around the Creek years before. He is immediately infatuated with her and pursues her unapologetically, culminating in their first dance together, despite Jen's reservations.
After helping Dawson film a scene at the ruins, they share their first kiss and start a relationship, which is quickly complicated by the revelation of Dawson's mother's affair and Dawson's hesitance to be truly emotionally intimate with Jen and let her support him. Dawson usually goes to Joey, which makes Jen feel like she's somehow playing second fiddle.
Despite Joey's clear feelings for Dawson and reprihensible behaviour towards Jen, they couple stay together – until Jen's ex-boyfriend comes to town and Jen starts to doubt everything, including her relationship with Dawson. After Jen breaks up with him, she dates Cliff but soon realises she wants Dawson back. Dawson, meanwhile has begun to realise his feelings for Joey and reacts coldly to Jen's advances.
When Joey and Dawson start dating Jen, at first, feels disillusioned, which extends to her view on her whole life in Capeside, greatly influenced by the loss of her Gramps. Continually in a funk and feeling estranged from Dawson and Grams, Jen starts hanging out with Abby Morgan, who encourages Jen to try and win Dawson back. This coallition makes Dawson uneasy, and eventually upset with Jen when she attempts to seduce him into coming back to her, although she is secretly devastated at her actions. Dawson rejects Jen and the two spend some time apart. Joey suggests inviting Jen to the school dance, prompting Andie and Dawson to happily match her with Jack, although Pacey and Joey are against it.
After Joey breaks up with Dawson, he starts noticing Jen's actions and looks out for her, when Chris Wolfe zeroes in on her. He's there for her when Jen crashes in his room being to drunk to go home and intervenes when a wasted Jen is hooking up with Chris and his friend. While Jen is livid at Dawson, she finally opens up to him about how horrible she feels and he comforts her. They start spending time together and Jen works as Dawson's producer on his upcoming project, where he is incredibly impressed by her skill. When Dawson laments his "too adult" mindset, Jen offers to teach him to just be a teen. This leads to them skinny dipping and Dawson kisses Jen, who rejects that they start anew as she feels good about their new friendship.
Even so, the two find themselves almost sleeping together one night, fueled by loneliness, heartbreak and Dawson's parents' imminent divorce. Jen admits to Jack that she still has feelings for Dawson.
- „When Dawson Leery climbs through my bedroom window it had better be for me”
- —Jen to Jack[src]
- „So here's what I'm gonna do. I'm gonna give you a hug, and I'm not gonna let go for a long time. I'm gonna tell you that I love you, which is a pretty good deal. It means that I'll do anything on the off chance it might make you a little less sad”
- —Jen to Dawson[src]