The only child of Theodore Lindley and Helen Ryan, Jen was introduced to the show in the first episode when she arrived from New York City to live with her grandmother, Evelyn 'Grams' Ryan, after her parents realized just how out of control she was. Jen initially provided a love interest for Dawson Leery, and the two dated throughout the first season, which caused tension between Jen and Joey Potter. Jen was the girl who grew up too fast and Joey was the girl who wondered what it would be like to do the things that Jen had done, so Joey was immediately threatened by the "City Girl". Jen and Dawson broke up when Jen's ex-boyfriend Billy came to Capeside to win her back. Billy caused immediate tension between Dawson and Jen, as Jen's past was coming back to haunt her and Dawson. Dawson in the heat of the moment basically called Jen a "Slut", and she broke up with him because, she had never been made to feel so cheap by anyone. By the end of the season she was regretting her decision to break up with him, and wanted Dawson back, especially as her sick Grandfather died.
After the Jen and Dawson breakup Jen became isolated from the rest of the main characters for much of the second season, especially with Joey as Jen's attempts to win back Dawson were stepping on Joey's toes. Jen became friends with Abby Morgan, the girl everybody hated, as she was seen as the Devil incarnate, and Jen and Abby often drank together. They both were intrigued by a sailor who was docked at Capeside and they both made moves on him; he liked Jen and this caused Abby's and Jen's short friendship to break up. Jen was caught with the sailor in her home by Grams. During her sophomore year Jen briefly dated a conservative Christian, but broke up with him after he was revealed as a homophobe; this came out while gay rumors were circulating about Jack McPhee. While Dawson was writing his script, she served as a mentor to him, in getting his inner youth out of him, and she was also a shoulder to cry on while his parents were going through their marriage troubles. She also again befriended the abrasive Abby Morgan, who died after falling off a pier while drunk. After Jen gave a brutally honest speech at Abby's funeral, Grams kicked Jen out of the house as Jen clearly showed a lack of respect, even though Grams had done everything she could to help her. Jen briefly stayed with the Leery's before she attempted a reconciliation with her parents, but they again rejected her. So Jen then went to live with Jack McPhee, as Andie and his father left for Providence to get Andie some help. But eventually they decided that they couldn't afford to live in the house by themselves, and so Jack and Jen moved back in with Grams and became close.
In the third season, although Jack moved out to live with Andie again, his relationship with Jen remained close - not unlike a sibling relationship. Jen attends the cheer leader tryouts purely to denounce the extremely unpleasant head cheerleader. This take an unwelcome turn when the cheer leaders who have become very discontented with their head, elect Jen as head cheerleader instead. Even more disconcertingly she is elected homecoming queen.
After Pacey is deemed the failure again by his family, he pursues a purely sexual relationship with Jen; both agree that there will be no emotion involved whatsoever. While trapped on Witch Island with Joey, Dawson and Jack, the two proceed to make out in the condemned church, which seems to be haunted by the spirits of thirteen girls who were burned alive there in the 1600s.
Pacey and Jen are nearly caught having sex in Dawson's room after he returns home from a dentist appointment. He finds Pacey on his bedroom floor apparently playing a video game. Pacey later must confess to Dawson of his secret arrangement with Jen after Dawson finds a condom on his bedroom floor. Dawson and Jen later join Joey and Pacey in ballroom dancing, and Dawson automatically assumes that Pacey is sleeping with Joey. When he and Joey find Pacey and Jen making out in the coat closet of the ballroom studio, everyone is shocked. Finally, Pacey and Jen decide their plan is no good and end the arrangement.
Jen's mother, Helen, unexpectantly shows up at Grams' house for Thanksgiving dinner. Although Grams tries to warn Jen, she finds out too late, walking in on Helen, who is dressed up and wearing pearls---just as Jen remembers her being before she was sent to Capeside. Dawson, unsure of whether or not to tell Jen, confronts Helen about the visit of Eve Whitman, Jen's half-sister. Due to Helen's request that Dawson not mention it ot anyone, Jen never learns of Eve's existence.
Jen's senior year comprised much of the fourth season. Though the third season had ended with Jen's unreserved (and public) commitment to Henry, Michael Pitt who had played Henry felt the role to be artistically undemanding.. Henry we learn in the first episode had accepted a football scholarship to a private school, broke up with Jen through Jack, devastating her. She became closer with Jack after the break-up and the two almost shared a drunken sexual encounter on the school ski trip. One of Jen's old acquaintances from her days on the New York party scene, Drue Valentine (Mark Matkevich), moved to Capeside to live with his mother, and brought an unhappy reminder of her past. The only child of Yacht Club owner, the Cruella DeVil-like Mrs. Valentine (and Joey's boss in seasons 3-4), Drue offered her Ecstacy, which Jen accepted from him, but never took. But after an in-depth conversation with an obviously disturbed Andie McPhee, Jen's friend took the ecstacy, which mixed with her medication caused her to gain a high fever, and could have killed her. This caused a massive rift between Jen and the rest of her friends, which was only healed after Andie told them that she was leaving for Italy. While her friends were all applying to colleges, Jen was reluctant to do so; Jack, with Grams' help, eventually applied to several schools for her, using previous school work for the essays. Though she considers returning to New York for school, she decides to go to Boston instead to attend the fictional Boston Bay College with Jack. During a read-aloud of her shrink's favorite author, Jen meets Toby, an admittedly gay teen whom Jack finds strongly unattractive. However, Jen gets along with Toby and soon learns that he has a 'thing' for Jack. After he makes it perfectly clear that he does not wish to take Toby to the gang's senior prom, Jen goes against Jack's wishes and tells Toby that Jack wants to ask him out. Jack gets even by setting Jen up with her old drug buddy, Drue as her prom date. While Jen and Drue seemingly reunite, Jen confesses to her old friend that she has changed her mind about attending college in New York.
In the season finale, Grams sells the house and decides to move to Boston with Jen and Jack.
The fifth season, which spanned Jen's freshman year in college, was somewhat tumultuous. Grams moved to Boston with Jen and Jack and the three lived together until Jack joined a fraternity, which (coupled with the alcohol abuse and academic decline it coincided with) created 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, However she found out that Charlie was cheating on her and she comically made him confess---with the help of Charlie's other girlfriend Nora, Jen convinces Charlie to "shut-up and get naked" just before locking him out of his dorm room in a hallway full of students. After the death of Mitch Leery, Dawson invites Jen to attend 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 losing his virginity to her, Dawson dives into a serious fast-paced relationship with Jen, but she breaks it off after realizing that it was the wrong thing to do.
During the gang's spring break trip to Florida, Jen finds Joey spending some quality time with her ex-boyfriend Charlie Todd. In trying to warn her, Jen's advice goes unheeded by Joey. In the meantime, Jen tries to have a serious conversation 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, ruin their plans. At first, Jen decides to spend the summer with her best friend, but when everyone collides at the airport in the finale, Dawson convinces Jen to go see her parents. She takes the next flight out to New York as Grams sneaks to Vegas with her boyfriend, Cliffton Smalls. Jen runs into "Damage Ink" director, Todd Carr on the plane; the same director who fired Dawson from his internship at USC.
During the sixth season, Jen embarked on a relationship with C.J. (Jensen Ackles) who she met at a campus cafe. Jack convinced her to call the helpline where C.J. worked to invite him to a Halloween party, but she forgot to mention to him that it was a costume party after he and his friend, David, show up in casual dress.
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. Upset, Jen leaves the situation, while C.J. gets into a fist fight with Pacey during a No Doubt concert.
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 retaliates by dumping C.J. before they have to host a Loveliness Questionairre with Drew Pinsky and Adam Carolla. When the pressure gets to be too much, Jen gives the hosting job to an ecstatic Audrey. Towards the end of the season, Jen calls on her mother Helen, (Mimi Rogers) to talk things out with Grams, and initially 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.
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 third 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. She leaves Amy in Jack's care and dies with Grams at her side.