The episode begins and Marty, Roscoe and Jeremiah are having dinner with Marty’s activist younger brother Malcolm. Turns out, he has resurfaced after 3 years. There apparently seems to be bitter rivalry between the two brothers. The check arrives and Marty has to pay, because Malcolm apparently has no money. Later at the office, Marty and team discuss their strategy for a dating site called Cupidchemistry.com. The website is basically their client and it’s their job to make it really successful. Julianne tells Marty she needs him to go to Chicago to rope in a really huge bank called US National as Gallweather’s client. Marty decides to take Clyde along with him to Chicago.
Jeannie isn’t very happy about it. Later in the plane, Clyde thanks Marty for choosing him to second over Jeannie. Marty and Clyde meet Carl, who heads US National. Carl is busy working out in his shots when they arrive to meet him at his office. Later, when Carl is explaining what the bank is all about to Marty and Clyde, Marty sees one of Carl’s balls hanging out of his shorts. He is visibly distracted by it and tries to look away. Carl’s secretary realizes this and makes sure the ball isn’t exposed anymore. The secretary Brynn tells Marty and Clyde that a team appointed by the bank has already done an analysis of the bank’s financials and other details.
They just want Marty and Clyde to go over the analysis. Marty and Clyde conclude that there is more to it than meets the eye. They conclude that Carl is doing all of this because he wants to run for office. Brynn reveals that Carl is actually planning to run for Governor, so they suspected correctly. Doug and Jeannie in the meantime are on their way to San Diego to meet the owner of the dating site. On the way, Doug convinces Jeannie to put her profile on the dating site and date a guy who the website suggests, fits her profile. She is initially reluctant, but in the end Doug manages to convince her to at least go for one date.
Clyde and Marty tell Brynn that the financials and the other details of the bank look good. Jeannie in the meantime arrives at a bar for her date. A little later, Cameron the guy the dating site selected for her arrives. The two apparently seem to hit it off and subsequently have a good time. “You are not at all what I expected” she tells him. He in turn asks her what she was expecting. “A socially awkward man-child with absolutely no game” is what she was expecting, she says. She asks him what is exactly wrong with him that he needs to “troll the internet” instead of dating girls in the real world. He says he doesn’t do too badly in the real dating world either.
She then reveals that she only came for this date as a dare from her friend. She then makes some jokes that Cameron finds in really bad taste and therefore he decides to leave. He walks away from the table, with a stunned Jeannie looking on. Brynn on the other hand calls Marty to her office and closes the door behind him. She pours him a drink and says she just wanted to hang out with him. The two, begin flirting with each other and Brynn begins taking off her clothes; Marty too helps her. She then begins taking off Marty’s clothes.
While they are making out Marty tries closing the deal. “As far as I am concerned, you and Gallweather are in” she tells him, realizing what he is trying to do. While they are at it, Brynn reveals that, Julianne had tried to talk her out of hiring Marty. Marty is shocked to hear this. Turns out, Julienne told Brynn there were other partners in the firm besides Marty who were capable of handling such a high profile banking institution. Marty isn’t at all happy with this revelation. “I told her that US National wanted Marty Kahn, period” Brynn says. Marty is really angry and has some angry sex with Brynn, which she apparently seems to love. Jeannie knocks on Doug’s hotel room door and tells him how much her date sucked.
Doug though, has found his match and is having a good time with her. He therefore asks Jeannie to leave, because he is about to have sex. Marty returns home. He asks Malcolm who is staying at his apartment, why he is here and what is it that he exactly wants. Malcolm pretends he is there because their father is sick, but Marty doesn’t buy it. Malcolm then reveals that, their father was in a bad car accident two weeks ago and this has worsened his ailment, which is why Jeremiah asked him to come home. Marty is shocked to hear this, because he had no idea about the accident. Marty walks to his room without saying much. The episode ends at this point.