Plot

When Marshall finds out he's the "reacher" in his relationship with Lily and not the "settler," he considers pursuing a sexy and cool female coworker. Meanwhile, Ted finds out Robin is a drinking game for his architecture students.

Robin thinks she's made it into the big time when one of Ted's students recognizes her from her stint on the morning show. Robin revels in the recognition so much so that she even drops by his class just so that more of his students will recognize her, which they do. Ted is later happy to learn that his students don't watch the show for Robin's interviewing prowess, but that her interviews are used for what they call the "but-um" drinking game. Ted can't help but rub Robin's nose with this information. But Robin thinks she has the last laugh on the matter. Meanwhile, Marshall is continually telling the exploits of his crazy new colleague, Jenkins. What Marshall fails to tell his friends is that Jenkins is a beautiful young woman, which transforms those crazy exploits into sexually provocative acts. Marshall, who was fearing Lily's reaction, is dismayed to learn that Lily isn't jealous when she actually meets Jenkins. After Jenkins kisses Marshall, he wants to use that act to make Lily jealous, but will Lily believe that Marshall can attract someone like Jenkins?—Huggo

Future Ted discusses the three places a 30 year-old New Yorker shouldn't be caught in: New Year's Eve in Times Square, Rockefeller Center during the holiday season, and any college bar. Ted and Marshall walk into a college bar, and Ted is worried about meeting his students there. Marshall returns to the bar on a regular basis to maintain his Skee ball high score, under the pseudonym Big Fudge.

Marshall then announces that they'll be meeting Jenkins (Amanda Peet), a co-worker, at the bar. He had told the gang a collection of hilarious stories about Jenkins (eating a jar of cherries with lots spilling over the shirt, seductively dancing behind one of the senior partners of the firm, topless stripper dancing on a table at a bar, peed out of a cab window), Ted imagining him as a fat funny-man. Barney then interjects with his desire to sleep with Jenkins, and Ted is surprised to find that Jenkins is a woman. Marshall says that the first time he told a Jenkins story, Lily assumed that Jenkins was a guy and Marshall never corrected her. Since then Marshall avoided pronouns when mentioning Jenkins.

The next day, Lily unexpectedly shows up for lunch with Marshall, and finds out that Jenkins is a woman. However, Lily is not at all jealous. Ted and Robin explain that it isn't Marshall's loyalty, but in every relationship, there is a "reacher" (a person who reaches for someone beyond their level of beauty), and a "settler" (a person who settles for someone below their level of beauty). Flabbergasted, Marshall forces Lily to classify herself as one or the other, and she, after much hesitation, says "settler." Marshall discusses with Ted, and wants to make Lily jealous. Ted says Jenkins is totally into him.

In an attempt to get Lily jealous, Marshall plans to show her how Jenkins flirts with him. While inviting Jenkins to go out again, this time with Lily, she kisses him. Marshall screams in anguish & runs home and apologizes to Lily (he says he stopped it right away as Lily is the only one for him), who jokes that she's going to go punch Jenkins in the nose, when she obviously thinks he's just lying to make her jealous. Jenkins meets Marshall the next day and finds that he told Lily about their kiss. She is embarrassed and confesses about being in a drinking game due to which she is drunk at 8 am in the morning. She plans to apologize to Lily, which Marshall knows will prove he is not just a "reacher."

Lily calmly listens to Jenkins' apology and promptly punches her in the nose, and continues beating her up, as Future Ted mentions that Marshall never tried to make Lily jealous again. Nobody kissed my future baby daddy, but me.

Meanwhile, Robin encounters fans of her pre-morning news show. When she met the boys at the college bar, one of Ted's students Scotty (Andrew Lewis Caldwell) comes over to tell her that he's a big fan of her work. Full of pride, she interrupts Ted's class the next day to loudly announce that she is the host of the show. After she leaves, the class explains that they are fans because her show comes on as their night of drinking is coming to an end (Her show is so early in the morning that the class is still at the bar from previous night), and her interjection, "but...umm" is the basis for a drinking game (whenever Robin says this, the students take a drink).

Ted and Barney test this game the next night, watching Robin's show, and get thoroughly drunk. After Robin continues to brag about her wide viewership (she offers to read one of Ted's lectures on air, saying the student might pay more attention since the lecture will come from a more entertaining source), Ted explains the drinking game. That night, his class invites him out to join their game (after Ted offers to pay). Robin gets her own back and decides to repeat the phrase "but...umm" excessively, prompting those playing the game to drink every time. This brings the drinking game to an end, forever. In another bar, Jenkins is also playing the same drinking game and is still drunk the next morning when she kisses Marshall.

During the next day's class, Robin interrupts again, startling the hungover group with a megaphone.