Liz develops a crush on Jamie, the new twenty-year-old coffee delivery man, and after some initial hesitation, she agrees to go on a date with him. Before the date, Liz gets cold feet, but she is encouraged to attend by Jenna, who declares Liz a cougar, a term describing "hot older ladies pouncing on their young prey". Liz agrees and goes on a successful date with Jamie; the pair agree to go on a second date. Prior to this second date, Liz goes to Jamie's apartment only to discover that Jamie still lives with his mother, who looks exactly like Liz.
In order to become a cougar herself, Jenna starts to date Aidan, a teenage freshmen at New York University. Jenna breaks up with Aidan when he starts to annoy her by wearing heelies and playing portable video games and acting like Jenna is his mother.
Frank begins to question his sexuality when he realizes that he has a crush on Jamie. He even tries to, unsuccessfully, rival Liz to go on a date with Jamie. Later, Frank realizes that the only man he is attracted to is Jamie and decides that he is in fact not gay.
Tracy is ordered to do community service in the form of coaching the Knuckle Beach Little League Baseball Team. Knuckle Beach happens to be "the worst neighborhood in New York". Hoping to inspire the team, Jack agrees to help Tracy and he donates uniforms to the team on behalf of the Sheinhardt Wig Company which is NBC's fictitious parent company. Jack replaces Tracy with Kenneth Parcell (Jack McBrayer) because he realizes that even with the newfound inspiration from both Jack and Tracy, the team is still failing. The team begins to revolt when they find out that Tracy has been fired. To counter this, Jack forms a coalition with Tracy and they replace members of the team with Grizz and Dot Com (Grizz Chapman and Kevin Brown). 
Frank: "Something just happened, Liz!"
Liz: "Come on, you read Boobs Magazine!"
Frank: "I want Jamie."
Liz: "You can't be gay for one person, unless you're a lady and you meet Ellen."
- Top Chef is a reality cooking show. Jack must be talking about season 3, which aired from June to October, 2007. However, Casey was a runner-up and was therefore never "voted off".
- R. Kelly is a musician who is known for allegedly having a sex tape that depicted him having sex with and urinating on an underage girl, and Michael Vick is a football player who was arrested for dog fighting (which was previously alluded to in Rosemary's Baby ).
- Simon Le Bon was the lead singer of Duran Duran.
- Liz makes a reference to Ellen, as in Ellen DeGeneres , who is a famously "out" celebrity.
- Zac Efron is a singer who was considered a teen idol after starring in the movie High School Musical.
- Mary Kay Letorneau was arrested for having sex with a her student, a minor named Vili Fualaau, in 1996.
- Harod and Maude is a movie about a young man who becomes involved with a 79 year old woman.
- Frank's hats say Ole, Right Boot, Got It, Handy Man, Burrito and Power Tool.
- Lutz tries and fails to get the writers to laugh at Frank for being "so gay". This is another in the ongoing gags that Lutz is himself gay.
- The sweater Frank buys Jamie is from H&M.
- Jack almost slips up and tells Liz about C.C., but he covers by saying that the company is his girlfriend.
- Jenna's song "Muffin Top" plays over the ending credits.
- Tina Fey - Liz Lemon
- Alec Baldwin - Jack Donaghy
- Jane Krakowski - Jenna Maroney
- Tracy Morgan - Tracy Jordan
- Jack McBrayer - Kenneth Parcell
- Judah Friedlander - Frank Rossitano
- Scott Adsit - Pete Hornberger
- Val Eemmich as Jamie
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- NBC Press Release – November 29, 2007