Michael is uncomfortable with his newly single status when he realizes he's actually on a date with new assistant district attorney Danielle Brinkman. Meantime, Paul meets the president of his fan club, Claudia Sacks, who has arranged the group's first meeting. And Carter and Stuart have a little too much to drink and end up in an awkward situation.

Mike butts heads with a hard-nosed new chief of staff appointee, Gabby Sanchez, who is unmoved by his best efforts to win her over. Meanwhile, Paul ponders taking his relationship with Claudia to the next level.

It's Valentine's Day, and Carter's old flame Spence wants to meet with him. Meantime, Mike goes on a date from hell with a beautiful friend of Nikki's, and Paul's romantic evening with Claudia becomes unforgettable for all the wrong reasons.

A major snowstorm hits Manhattan, causing a chain reaction of mishaps at City Hall. Mike desperately tries to meet his longtime crush on her last night in the city; Paul accidentally offends the Mayor on the radio; Carter and Stuart are locked in the boiler room; and a nudist is on the loose in the Mayor's office.

Michael discovers that his new girlfriend, Gayley, is paying for law school by moonlighting as a stripper. Meantime, Claudia catches Paul in a lie, and Nikki plays mind games with Stuart.

It's damage control time when the Mayor's inept new sign-language interpreter inadvertently offends the deaf community, and Michael rushes to appease one of its leaders, Sarah Edelman. Meantime, Paul is worried that Claudia wants to move in permanently.

Despondent over his separation with his wife, the Mayor decides on a whim to take a road trip with Paul, leaving Mike in charge of New York City and scrambling to find out where they went.

While acting as the Mayor's divorce lawyer, Michael is attracted to his opponent, Laurie Parres. Meanwhile, the press thinks Paul has suffered a nervous breakdown, so Michael enlists a psychiatrist, Dr. Benjamin, to pronounce Paul sane. But his plans go awry when Dr. Benjamin unexpectedly commits Paul to an institution.

While jogging in the park to support the Mayor's fitness initiative, Carter is apprehended by the police, who mistake him for a mugger. To Carter's chagrin, Michael wants to downplay the incident for political reasons, while Carter wants to publicize his own outrage. Meanwhile, Paul becomes paranoid that he himself is a racist; and James struggles to pull off a successful date with the new supply girl, Katie.

The Mayor's free-thinking daughter, Meg, with whom he has a somewhat strained relationship, puts the ""bare"" in bareback when she disrupts a rally with hansom-carriage drivers in Central Park to draw attention to her animal rights stance--and not coincidentally, herself. Meantime, the gang tries to reunite a needy Paul with ex-girlfriend Claudia, but he's smitten with his new pen-pal.

Faced with the prospect of spending Valentine's Day alone for the first time in eighteen years, Mike is thrilled when old flame Laurie steps back into his life. But he doesn't know what to do when she discovers a ring Mike was holding for Paul, and assumes it's for her. Meanwhile, Paul plans to propose to Claudia.

When Laurie accepts Mike's proposal, he begins to worry that they are too different. Meanwhile, Paul struggles to get the courage to propose to Claudia, and various staff members fantasize about what their life would be like if they married Mike.

Mike suggests the staff undergo drug testing to demonstrate the mayor's new anti-drug campaign. But after he accidentally gets high while visiting some Native Americans, he risks failing the drug test that he initiated.

The staff prepares for Paul and Claudia's bachelor and bachelorette parties as the city prepares to unveil a new statue that it commissioned. The girls play ""I Never...."". Paul's party is in the office because the Mayor can't go to strip clubs. The new statue, called ""The Bird,"" is, you guessed it.... The girls think a visiting priest is a stripper because of a prank pulled by Stuart. James and Carter go to the hardware store and it is robbed with them in it. Mike is trapped in the store too, after he goes checking for James and Carter. Stacy sends the guys the male stripper Stuart canceled for the girls.

Stuart lobbies to become Carter's roommate. After Carter's apartment is robbed, he must let Stuart stay. A rat on the loose in City Hall wreaks havoc on the staff and Paul's cat.

The Mayor has a stuttering problem. And Mike has a big problem when he promises to coordinate Paul and Claudia's wedding but discovers that the church is also booked for a funeral at the same time.