|“||I love to see a man drown his sorrows. It’s so sexy.||”|
Kelly is a member of the Donovan Family.
Kelly Donovan grew up in Mystic Falls and she was best friends with Elena and Jeremy's mother, Miranda Sommers-Gilbert, while in high school. During that time, she dated a guy who she described as "not impressive," who later became a plumber. Kelly would later win a date with this same man in a charity raffle. She used to babysit Jenna Sommers, who was Miranda's younger sister and they became good friends who partied together once Jenna was old enough. She and Miranda remained good friends after Miranda married Grayson Gilbert, and their children Matt Donovan and Elena Gilbert sometimes used to share a crib when they were babies. Kelly also had a daughter, her oldest child who was named Vicki. Several years later, Kelly left Mystic Falls with her boyfriend Pete and left Matt and Vicki to fend for themselves.
Sometime before she left town, she had been working at the Mystic Grill; however, she was fired when Kelly slept with the boss' boyfriend. She was gone for an unknown amount of time with her boyfriend Pete, and she eventually returned to Mystic Falls after Pete supposedly broke up with her. When she entered the living room, she found her son Matt on the couch, making out with his new girlfriend, Caroline Forbes.
She was seen to be extremely immature, to the point that it was up to Matt to continue paying their bills with his paycheck from working as a busboy at the Grill. After her return to town, she had hooked up with many men who appeared to be half her age. After Matt asked his boss to get his mother's job back, Kelly went to the Mystic Grill for an interview with the manager, but was ultimately stood up. It was then that she met Damon Salvatore and was reunited with her old friend Jenna. Kelly and Damon flirted throughout the night until Damon brought her home with him to the boarding house. They began making out in the foyer until they were interrupted by Matt, who walked in on them in the act and who quickly became angry at his mother for acting like a teenager while he was forced to be the adult in the family.
Kelly openly disapproved of her son's relationship with Caroline, even telling her face to face that she thought Caroline was fake and that she did not like her. In Under Control, Kelly got drunk at a party at the Lockwood Mansion and made out with Tyler Lockwood, which was once again interrupted by Matt catching them, causing Matt to lash out at Tyler and get into a vicious fight. When Kelly returned home, Matt had packed up all of her things and had insisted that she leave the house, as he was tired of continuing to give her more chances when she didn't deserve them. She was upset, but left as she was asked, and has not returned to town since.
- Lost Girls (Mentioned)
- 162 Candles (Mentioned)
- History Repeating (Mentioned)
- Unpleasantville (Mentioned)
- A Few Good Men
- There Goes the Neighborhood
- Let The Right One In
- Under Control
- The Sun Also Rises (Mentioned)
- Postcards from the Edge (Mentioned)
- Kelly is a Gaelic name, meaning "war" or "strife." This could be a nod to the fact that her life was full of strife.
- In a deleted scene from the episode A Few Good Men, a man died right after making out with Kelly. This indicated that she was supposed to be a succubus, but, in the end, the writers decided not to pursue that storyline. Ironically, (or fittingly), Melinda Clarke played the Siren on Charmed, who was also a demon who killed men by incinerating their lungs while kissing them.
- Matt stated that Kelly made out with a guy (Damon Salvatore) who was half her age, but the irony is, though Damon is younger in physical years, he is about four times older than Kelly in chronological age due to him being a vampire.
- Kelly made out with Tyler Lockwood however, who is also half her age.
- Kelly never shared a scene with her daughter Vicki during her time on the show. However, Melinda Clarke and Kayla Ewell did have to take a photo together for the episode A Few Good Men.
- Kelly was one of the parental figures in the series who is not a member of the Town Council. The others are: Abby Bennett Wilson and Rudy Hopkins.
- Kelly is the only parent in the series who doesn't know about the supernatural world.