Ninety days have passed since Gordon broke up with Dana, and Casey is trying to find the right time and method to approach her romantically. Dana is worried about Isaac's ability to work since returning from his stroke. Natalie and Jeremy argue over the possibly of her taking a job in Texas.
A rumor is spreading through the studio that the network has hired a ratings expert for the show. Casey makes plans for his first date with Dana. Dana attends a biker-themed bachelorette party and has an epiphany. Dan is invited to Hillary Clinton's fund-raising breakfast. Sam Donovan arrives.
The presence of Sam Donovan has everyone on edge. In spite of Casey's best efforts, Dana will not budge with regards to her "dating plan". Network executives meet with the Sports Night staff with suggestions. Sam Donovan tells the network executives about Cliff Gardner.
An internet poll asks viewers who is cooler - Dan or Casey? Casey intends to win this poll by any means necessary, and recruits Jeremy to help. Relations between the staff and Sam Donovan begin to thaw. Dana goes on a date with Cab Calloway (no, not that Cab Calloway). Natalie is emailing Jeremy's sister.
Jeremy convinces Dana that he is qualified to eliminate any potential Y2K problems from the computers as they approach the millennium. The "dress rehearsal" test of his changes doesn't go without some problems. Dan meets a woman at a bar who asks her to call him. However, since the woman is a psychologist, Dan is not exactly sure if her intent was romantic or professional.
Dan continues to see Abby, hoping to get to the bottom of his escalating emotional problems. Casey interviews Shane McArnold - an old friend and professional baseball player who has signed with the New York Yankees. Dana is tickled pink when Shane makes a fool of himself and refuses Casey's request to edit the interview. Natalie is alarmed that the Vatican has denounced the existence of hell as an actual "place".
Songs: Katrina And The Waves -- Walking on Sunshine
Dana cannot contain her pride for her brother who got two sacks while playing in a Monday night football game. Jeremy is in charge of the irresponsible cousin of a network executive, and must learn to take a hard line with him. Sports Night investigates a drug scandal involving several pro athletes. Dan continues to struggle with emotional issues.
Dana must deal with the recent news that her brother Kyle has been taking anabolic steroids and will be suspended from the team. The staff buys "Secret Santa" gifts for each other and discuss who should be "Athlete of the Year".
Per the rules of Dana's dating plan, Casey goes out on a date with a girl named "Pixley". The staff is trying to research news for tomorrows show, which is short by 42 minutes. Jeremy has been nominated for an award and is having problems writing a suitable acceptance speech.
Dan is excited to learn that Isaac attended a specific historic baseball game in 1952, but Isaac is reluctant to talk about it. Casey bumps into Pixley and writes his phone number on her hand. Dana finds about about this and is concerned.
Sports Night provides special coverage of a boxing match. When the scheduled ring-side color commentator gets sick, they must recruit a man who is only marginally qualified for the job. Dan's father visits him at the studio, but their reunion isn't as warm as Dan would have liked. When the fight ends in a knockout after seven seconds, Dan and Casey have to fill for an hour and a half. Dana begins to regret her "dating plan" for Casey.
Dan wants to change his name to "Daniel". Sam Donovan is driving Dana crazy. Michael Jordan would like to announce his new line of cologne on Sports Night, but the staff is concerned that they won't have the opportunity to discuss sports with him. Casey goes to his son's class to give a presentation of sorts.
One hand washes the other as everyone's plans depend on favors from each other. Dana inherits a revolutionary war rifle and is less than thrilled about it. Natalie gets on the list to a hot nightclub, but Jeremy doesn't share her excitement. Casey has to work with a substitute anchor who's off-air girlfriend problems affect his on-air performance.
After experiencing some vision problems, Casey goes to an ophthalmologist. Since he had to have his eyes dilated, he has to wear dark glasses and can't see. Natalie and Jeremy break up. Sports Night is subpoenaed to turn over videotape of a riot that occurred on a nearby street. It's Sam Donovan's last day and Dana wants to get him a cake.
With the unpleasant breakup of Natalie and Jeremy, relationships in the studio are strained. The staff of Sports Night create teams and play the game "Celebrities". Jeremy meets a girl in a bar who turns out to be a porn star.
The episode is told by Dan to his therapist. Sports Night is covering the tape-delayed broadcast of a track and field event in New Zealand. Jeremy emails an adult film actress that he met recently in a bar. Dana goes to church.
It's football draft day, and the staff is making predictions on who will be picked. Word starts to spread that Jeremy is dating a porn star. Dan has plans to go golfing with a notable pro golfer, but if it rains at Indian Wells, he'll have to remain in the studio for additional draft day coverage.
Sports night continues to cover the professional football draft. Tensions are strained between Casey and Dan. Jeremy's new girlfriend is stopping by the studio and since he doesn't want Natalie to know that she's a adult film actress, he tells her that she's a choreo-animator.
Reductions in Olympic coverage appear to be harbinger of future staff cutbacks at Sports Night. Jeremy plans a Jewish Sader at the studio and invites several of the non-Jewish staff to participate. The anchors are at odds after Dan's recent on-air embarrassment of Casey. The cool relations between Jeremy and Natalie begin to thaw.
Dan has hired a publicist, but is a little apprehensive about some of the places he is asked to go. Natalie has a job interview with Saturday Night Live. Casey and Jeremy monitor CSC's stock online. Isaac's new grandson visits him. Continental Corp is put up for sale.
The discussion among the staff is centered primarily around who is bidding to buy CSC, and the very real possibility that they may all be out of a job soon. Dan is shocked to discover that Kim is actually NOT his secretary. Dana meets a man at the bar who seems to know quite a bit about the current bidding situation with CSC.
A company named "Quo Vadimus" puts an 11th-hour stock bid on Continental Corp. Rebecca may be coming back into Dan's life. Dana discovers that the mystery man in the bar is actually the owner of Quo Vadimus. He purchases CSC and tells Dana that he will be keeping Sports Night on the air.