Lily, Barney and Robin attend a high school prom to scout out a potential band for Lily and Marshall’s wedding reception. In order to get in Lily and Robin pretend to be the dates of two kids who were going alone. Ted and Marshall are back at the apartment where they are preparing the invitations to be sent out.

Robin is nominated to receive an award for a news report and everyone needs a date to take to the show. Barney introduces Ted to Mary as a date that Ted can take to the show. Originally Ted is opposed to the idea of just trying to save face in front of Robin but when she shows up with a date he changes his mind. Robin asks Mary lots of questions, and Ted begins to really like Mary, despite her occupation.

Robin, who is very lonely, asks Ted to come over to her apartment after 2 A.M., but he isn’t sure if he wants to go as he has a phone call on the way over with his friends, and with Victoria on his mind

Marshall interns at the corporation where Barney works and Lily finds that he is becoming a shallow jerk as he tries to fit in with his crude fratty coworkers. Meanwhile, Ted feels guilty when he receives several gifts from Victoria (Erika Singh) while he hasn’t sent her anything.

Things are going great with Ted and Victoria’s relationship, but when Victoria is offered her dream job, the couple have to make serious relationship decisions. Meanwhile Marshall and Lily set out to purchase their wedding outfits and find out that none can afford what they bought.

A mysterious tape arrives for Barney from one of his numerous ex-girlfriends, and the entire gang watches it. But, in order for them all to find out how she broke Barney’s heart and made him into a suit-wearing bachelor, everyone must share their most embarrassing moment.

After agreeing to take things slowly and not have sex for a month, Ted and Victoria decide that they have waited long enough.

Ted finds a new woman at the wedding. They want to remember the evening so they don’t exchange last names or numbers; but Ted takes a big fall when he tries to find out her name.

Robin accepts Ted’s invite to a friend’s wedding, but thanks to Ted, the couple may never make it down the aisle.

Ted rents a limo to take the gang out to sample five New Year’s Eve parties in a quest to find the perfect celebration.

After being forced into knocking back 5 shots, so he will stop thinking, Ted goes on a partying rampage. The next morning he wakes up with a woman in his bed, but he does not know who it is. So he turns to his friends to try and piece the night together and work out who the woman is in his bed.

Ted and Robin are surprised to run into Barney when they volunteer at a homeless shelter on Thanksgiving. Lily is on the brink of freaking out when she goes to Thanksgiving dinner at her future in-laws house.

As Lily becomes more of a permanent fixture in the apartment, Ted feels like he is being edged out of the mix by his engaged roomies. Petrified of being left alone and homeless, Ted tells Marshall that when he and Lily are married, he wants the apartment. The problem is that Marshall wants to keep the place too, so they settle it like real “grown-ups” — launching into a sword fight that leaves one man down for the count.

When a matchmaker with a 100% success rate turns Ted away because he is not compatible with any of the available women in her database, he is still determined that he is going to find his match. After getting information from the matchmaker’s computer, Ted pays a visit to a very cute, but taken, dermatologist in an effort to prove the prediction wrong that there are no women out there for him. Meanwhile, Marshall and Lily are obsessed with ridding their apartment of a critter.

Ted makes his yearly pilgrimage to the rooftop Halloween party in search of a girl dressed as a pumpkin who he met years ago. Meanwhile, Robin is dumped after driving her new boyfriend away with her independent ways.

Ted and Barney start checking out the club scene with their friend Robin, whereas Lily and Marshall try to participate in some more “grown-up” activities, as they draw slowly nearer to their wedding.

Ted’s outlook on his continuing search for love is altered when he rediscovers a shirt that has not seen daylight in years. Meanwhile, Barney amuses himself by coaxing Robin into sacrificing her job by saying completely outlandish things on air live for a cash reward.

Ted agrees to let Barney spice up his love life, and ends up on a crazy adventure of flying to Philadelphia, encountering the law and visiting the Liberty Bell.

In a desperate attempt for a second date, Ted invites Robin to a party he is throwing. However, she doesn’t show up and he keeps throwing parties in the hopes she will finally arrive.

When Ted’s best friend Marshall proposes to his girlfriend, Lily, Ted realizes he’d better get a move on if he hopes to find true love. Ted soon meets Robin in a neighborhood bar, immediately becomes smitten and scores a first date. But when Ted can hardly wait to see her again, his eagerness threatens to scare her away.

Nucky plans to relocate to Manhattan; Margaret impresses Nucky and a grain company stockholder.

Nucky tries to hold onto his assets in Atlantic City; Willie and Eli become involved in Nucky’s war.

Federal agents enlist the help of Eli and Van Alden to take down the Capone organization.

Chalky returns to Atlantic City; Nucky arranges a meeting with Maranzano; Eli reunites with June.

Nucky and Margaret find common ground in Atlantic City; Luciano encounters an old adversary; Sally Wheet makes a payment in Cuba; in 1884, young Nucky moves up the Commodore’s ladder.

Chalky heads in a new direction; Margaret finds herself in a quandary; Nucky hosts a prospective partner from Boston; Luciano and Siegel meet with Narcisse in Harlem; in 1884, young Nucky flirts with a girl.

Nucky pays a visit to Johnny Torrio; Eli and Van Alden must recoup money lost during a federal raid by Eliot Ness; Willie has a job interview; in 1884, young Nucky deals with the death of his sister.

Nucky reminisces about catching the Commodore’s eye; Nucky joins Sally Wheet in Cuba; Margaret finds herself in the hot seat; Chalky tries to extricate himself from a difficult situation; Lucky Luciano sets a bold plan in motion.

Eli braces for the worst as Agent Knox launches his plan to bring Nucky down. Capone and Torrio reach an agreement in Cicero. Chalky looks to settle scores. Richard steps forward to save Tommy, at Gillian’s expense

Nucky takes inventory after being warned of a skunk in his cellar. On the lam following a close call, Chalky and Daughter take refuge outside Wilmington with Oscar Boneau, his mentor from years ago. Gillian considers selling her mansion and starting a new life with Roy Phillips.

Nucky enlists Eli and Agent Knox to check the cargo in the Florida shipments; Margaret considers making a deal with Rothstein; Capone grows suspicious of Torrio; Nucky faces a dilemma.

Nucky refuses to back Chalky in a conflict; Gillian makes her custody case in court; Van Alden stands up to Capone and comes clean to O’Banion; Rothstein tries to make a trade.

Nucky’s shipment from Florida arrives with some unexpected cargo. Eli is backed into a corner after Agent Knox uncovers some new dirt on the Thompsons. After talking things over with Nucky, Willie reconsiders his recent life choices. Chalky throws down the gauntlet toward Valentin Narcisse, upholding his leadership on the Northside.

Eli confronts Nucky after Willie makes an unpopular decision. Margaret has a surprise encounter at her job on Wall Street. Joe Masseria orders Lucky Luciano to return to Tampa and deal with Vincenzo Petrucelli. Gillian goes cold turkey, with Roy Phillips’ help. Still seething over his brother’s death, Al Capone tries to get Johnny Torrio to turn on rival gangster Dean O’Banion. As Chalky White and Daughter Maitland’s relationship deepens, Valentin Narcisse exerts his control over Dunn Purnsley and the Northside.

Nucky heads to Tampa to work out details of his land deal with Bill McCoy; Richard Harrow returns to Atlantic City; Agent Knox tries to gain Eli’s trust; Chalky takes out his frustrations on Daughter Maitland.

Nucky heads to Philadelphia; Agent Knox detains Eddie Kessler to obtain information about Nucky’s organization; Gillian tries to score a fix; Van Alden is recruited by the Capones.

Nucky gets to know Arnold Rothstein over a card game, and sizes up an unexpected partner for his Tampa land deal. A newly promoted Eddie Kessler gets detoured after making a train-station delivery. When one of their collectors is incapacitated, Al and Frank Capone decide to finish his route, enlisting a reluctant Van Alden to tag along. Agent Knox fills Hoover in on the Thompson operation, vowing to exploit Nucky’s weakest link. Chalky is intrigued by Daughter Maitland’s presence. Dunn Purnsley goes to Harlem, and is courted by Valentin Narcisse. Willie and his college roommate, Clayton, carry a practical joke too far.

Nucky has reservations about investing in a Tampa land deal engineered by transplanted bootlegger Bill McCoy. While there, he meets speakeasy owner Sally Wheet. Valentin Narcisse books a sexy jazz singer, Daughter Maitland, to perform at the Onyx, and gauges Dunn Purnsley’s allegiance to Chalky. Willie, Eli’s son, turns to Mickey Doyle and his bootleg warehouse to elevate his social standing at college. Gillian agrees to pose as Roy Phillips’ wife to impress a possible partner. Harrow tries to bury his past, though not before taking care of some unfinished business with Emma.

Now working as a “delivery man” for Dean O’Banion, Van Alden is ordered to keep tabs on Al Capone, joining the ascendant mobster to help keep Cicero voters “informed” at a political rally. Dr. Valentin Narcisse arrives in Atlantic City, clashing with Chalky and Nucky over the loss of an employee. In Washington, Agent Knox aligns himself with J. Edgar Hoover, acting director of the Bureau of Investigation. Harrow fails to finish a job in Milwaukee, while Eddie demands a promotion after 11 years of service. With a business opportunity on the horizon, Nucky departs for Florida.

Following his battle with Gyp Rosetti, Nucky makes a peace offering to Joe Masseria while working the odds with Arnold Rothstein. While Chalky is busy running the Onyx Club on the Boardwalk, the impulsive Dunn Purnsley clashes with a booking agent. Fresh-faced Federal Agent Warren Knox arrives in Atlantic City to learn the ropes from Agent Sawicki. Gillian seeks custody of her grandson, Tommy, while trying to find a “good” man to keep the Artemis Club afloat. Eli’s college-age son, Willie, turns to Nucky for career advice. Al Capone enlists his brothers, Frank and Ralph, to help him expand his business in the Chicago suburb of Cicero. Richard Harrow returns to his violent ways.