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- „You can't rely on somebody else to make you feel alive. It's an inside job.”
- —Jen to Pacey[src]
Jen grew up with her parents in New York and her parents sent her to live with her conservative Christian grandmother (whom she calls "Grams"), and they often clash. As the series progresses, Grams loosens up and becomes more tolerant and loving.
The only child of Theodore Lindley and Helen Ryan, Jen is introduced in the pilot when she arrives from New York City. Jen fell for Dawson Leery, and the two date throughout the first season, which causes tension between Jen and Joey Potter. Later, Jen falls back into her bad girl ways, befriending the school's bad girl Abby Morgan, attempting to steal Dawson from Joey, and getting drunk at parties. After she befriends Jack, another outsider, she begins to feel loved and during third season, she and Joey become friends.
Jen arrives in Capeside the day after having an big fight with her father, which is the last time she will see him in 3 years. She meets Dawson, Pacey and Joey, but doesn't share the reason why she's in Capeside, instead putting up a sunny demeanor. Although her fear and bewilderedness at her life shows itself in her hesitation to date Dawson, whom she has quickly developed strong feelings for.
To find some stability, seeing as how her Gramps is comatose and her Grams is not full of loving kindness, Jen attempts to strike up a friendship with Joey, unaware that Joey is in love with Dawson. Although Joey attempts to keep Jen at arms length, and is often rude and bullies Jen, Jen continues to try and befriend Joey. After realising Joey's feelings for Dawson, Jen abates but also learns that Joey actually likes her.
Faced with her ex-boyfriend from New York suddenly appearing in Capeside, Jen's memories of her life with her parents come flooding back and she breaks up with Dawson and says goodbye to Billy for good. Life in Capeside this way proves lonely and Jen quickly wants Dawson back, amidst her Gramps awakening from his coma, only to pass away, leaving the already heartbroken Jen devastated.
These events break Jen's will to create some semblance of a life filled with love for herself and she strikes up a 'friendship' with Abby Morgan, which is all about getting guys and partying. Her heart isn't in it and Jen occasionally re-circulates with Dawson, Joey and Pacey, as well as befriending Jack McPhee. Jen also eventually finds a connection with his sister, Andie. Unable to find the balance, Jen eventually spirals when Abby accidentally drowns in a drunken stupor and Grams throws her out of the house. Jen moves in with the Leerys and phones her parents to see if she can return to New York, to no avail. Luckily, Jack is there to support Jen in this trying time and eventually Jen approaches Grams about starting over – with Jack in tow.After a summer of living together with Grams, Jack and Jen have become best friends. Jen becomes Head Cheerleader and Homecoming Queen, after a mock cheertryout intended to ridicule the institution. In the process, a freshman named Henry is smitten with her, but she rejects him, leaving her feeling bad for hurting him and soured with love. After Pacey breaks up with Andie, he too, is destitute and while trapped on Witch Island with Joey and Dawson, the two proceed to make out, deciding to pursue a friends-with-benefits relationship. Jen's mother, Helen, unexpectedly shows up at Grams' house for Thanksgiving dinner. Jen is unsure how to handle her mother's appearance, and becomes almost inconsolable after her mother relays that Jen has a half-sister, making her mother's actions of sending Jen away hypocritical. They reach an understanding, and Jen feels a sense of relief moving forward. Pacey and Jen ultimately call quits on the friends-with-benefits situation before anything happens.
Henry and Jen's relationship is the main focus of her storylines, as well as her increasingly loving relationship with Grams, and the new experiences that Jen have with Henry, who provides her the kindness, respect and love that she had thus far never had, and been afraid to experience.
"I think, after all this time, you finally believe that you really do deserve to be loved." – Grams to Jen in Season 3.
In spite of Jen's unreserved (and public) commitment to Henry, he leaves Capeside for a football scholarship at a private school and early in the season breaks up with Jen through Jack, devastating her.
Henry moves away and breaks up with Jen at the beginning of the fourth season indirectly (by telling Jack), causing her to feel depressed. She gets into one bad situation after another at school because of Drue Valentine, a former friend who used to do drugs with her when they both lived in New York together.
She starts seeing a therapist to speak about all her issues from her past, which culminates in a visit to her father. We learn during this visit about the incident that escalated her wild behavior - when she caught her dad cheating on her mother and sleeping with a teenage girl.
Grams moves to Boston with Jen and Jack and the three live together until Jack joined a fraternity, which creates a rift in his relationship with Jen. While at Boston Bay Jen briefly dated musician Charlie (Chad Michael Murray) and ran a school radio show.
After the death of Mitch Leery, Dawson invites Jen to the Hookset Film Festival in New Hampshire after he learns that his father entered him in the competition, using his film about now-deceased-director A.I. Brooks. Dawson wins first place, and jokingly thanks "his girlfriend Jen Lindley".
After sleeping together, Dawson and Jen begin a relationship, but she breaks it off after realizing that it doesn't feel right. During the gang's spring break trip to Florida, Jen finds Joey spending time with Charlie and tries to warn Joey about him and speaks with Jack about his drinking problem.
At the end of the season, Jack relays to Jen that he's passed all of his classes, and the two friends prepare to take a vacation to Costa Rica. However, an unexpected phone call from Jen's parents in New York alter their plans. At first, Jen decides to spend the summer with her best friend, but when everyone collides at the airport in the finale, Jen ends up going to New York.
Jen meets and becomes interested in C.J. Joey's roommate Audrey ends up sleeping with C.J. when she gets drunk before a gig with Emma's band at Hell's Kitchen. Jen learns of C.J.'s sexual misadventures only after he tells her that he no longer dates. In the meantime, Grams is diagnosed with breast cancer and decides not to tell Jen. When Grams gives in and tells Jen of her illness, Jen dumps C.J., who refuses to let her off the hook until she tells him that Grams is sick and he consoles her. When the pressure gets to be too much, Jen calls on her mother Helen (Mimi Rogers) to talk things out with Grams, mainly so Grams can tell her own daughter about the cancer. Eventually, Grams' boyfriend, Bill Braxton (also C.J.'s uncle) breaks the ice and tells Grams that she can't give up the fight. Grams, Jen, and Jack decide to move to New York to live with Jen's mother while Grams undergoes treatment, and Jack and Jen end up attending NYU.
In the two-part series finale, set in 2008, the gang learns of Jen's fatal heart condition, pulmonary congestion, after she faints during Gail Leery 's second wedding. Jen, now the single mother of a one-year-old daughter, Amy, ends up hospitalized and reveals to Jack, her best friend, that there is nothing to be done to save her. Leaving Amy in Jack's care, Jen dies with Grams at her side on May 14, 2008.
- „Until I can look at myself without judgment or condemnation, I'm not ready for anybody – let alone you”
- —Jen to Henry[src]