Career Night was an event that occurred during a full moon in December 2009. It was held in the Mystic Falls High School. Students attended to get an idea of what careers they would pursue after high school. Before the event Damon fought with the newly turned vampire, Logan Fell.
During the Career Night, Tyler and Jeremy got into a fist fight. Alaric Saltzman and Mayor Lockwood luckily were able to separate them. Afterwards, the Mayor wanted Jeremy and Tyler to fight outside and "handle this like real men", which shocked and embarrassed Tyler and Jeremy, who had no interest in fighting each other. As the Mayor pushed them to fight, Alaric confronted him and was able to get him to leave the boys alone. At the end of the night, Jeremy tried to smooth things over with Tyler, after seeing the abusive ways his dad treats him, to which Tyler got extremely angry and punched Jeremy again. Jeremy angrily asked Tyler what his problem was, and Tyler, looking remorseful, told him he didn't know. As he walked away, the camera pans to the full moon, indicating that it may have had an affect on his mood swings and furthering suspicions that Tyler is a werewolf.
Logan Fell came to the school and ran into Sheriff Forbes, confronting her, as he believed her to be responsible for his death and it's cover-up. He later kidnapped Caroline to get even, and called her mother to tell her he was going to turn Caroline into a vampire. Damon and Stefan were able to save her, and Damon was about to kill him when Logan mentions that he's not the only person who wants to get Katherine out of the tomb, catching Damon off guard. When the Sheriff approaches Damon and Logan, Damon tells him to make it look convincing; Logan ends up kicking Damon against his car and speeds off, and Damon apologizes to the Sheriff for not being able to take him. Later that night, Alaric, who is interested in Jenna, Logan's ex-girlfriend, confronted Logan at the Fell Warehouse. Logan Fell attempted to kill him, but Alaric staked him before he got the chance, revealing Alaric's prowess at vampire-hunting.
- When Matt Donovan 8 years old, he wanted to be an astronaut.
- Stefan Salvatore wanted to be a doctor but he couldn't because of the Blood involved.
- Elena Gilbert wanted to be a writer because of her mother and her diary.
- Caroline Forbes decided for Broadcast Journalism during the Career Night which she's shown to be in 2016 flah-fowards.