Liz finally got the nerve to end her relationship with Dennis. Jenna wanted to take Liz out to celebrate her break up. Liz was so old-fashioned; she thought she would be going to a disco, Jenna realized she had her work cut out for her.
Jack called Liz because he was becoming paranoid that his lady friend was cheating on him. Liz didn't have time to talk; she was too busy waiting outside a bar for Jenna to arrive for their girl's night out.
Once Jenna arrived at the bar, if was obvious that Liz was new to the bar scene. The drunker she got, the more awkward she got around guys. Jenna retired the night early to avoid more embarrassment from Liz.
Toofer and Tracy were getting on each other's nerves and the tension was building. Tracy thought Toofer was a sell out and not a real black man. He ended up calling Toofer a racial slur and Toofer filed a harassment suit against Tracy. Liz and Jack tried to smooth things over between the two guys.
Dennis surprised everybody and showed up to Liz's writers' meeting. He wanted to read her one last letter before he got out of her life forever. He wanted her to know that he would always love her. When he left, the TGS staff all thought Liz should give Dennis another chance.
Jack ran into a heartbroken Dennis in the bathroom. Jack sought advice from Dennis on how to handle his lady friend, who everybody suspected to be Condoleezza Rice. Jack took Dennis' words of wisdom very seriously. Jack later told a shocked Liz that he judged Dennis too early and actually liked him.
Tracy and Toofer both had to attend sensitivity training because of their verbal spat. They hashed out the reasoning behind their behavior while other's watched on. Tracy stopped the argument and thought the two had a great sketch idea for the show. Later on, the sketch idea got dropped in favor of a bit about Star Jones.
Liz came home that night to find her apartment spotless and a note from Dennis on her coffee table. The note was to let Liz know that if she got sad, there was a meatball sandwich in the fridge for her. She began a list of the pros and cons to dating Dennis. The final straw was when Dennis was caught on television with a 16-year-old girl! She dumped him for good!