We get a story of six friends who are struggling to live in New York. We meet Dawnie whose birthday it is. She's a 26 year old virgin and still struggle to find love; her college flame Ty comes back into her life when Sam runs in to him. Sam who is a D.A. Assistant tries to make it through another day when her boss Vince teases her about her ascent. Sam is good friends with Vandy, her former beau, bar owner, and a struggling song writer. Jesse is on the conquest to find her perfect man but doesn't seem to meet him anytime soon. Jesse is close with the hunk super soap opera star, Russell who is gay but hides it to protect his ""hunk"" image.

What's in your pocket? Dawnie is still working on her thesis. She claims things in your pocket is a window to someone's soul. Jesse finds a guy who dates Jewish women only but Jesse's not Jewish. She lies to him just to go out with him. He then dumps her because he thinks she doesn't want a relationship. Ty gets fired from his job, and Russell makes him move in with him and Dawnie. Dawnie and Ty have little chat and she ""accepts"" him as her friend again.

After being fired from his job, Jesse hires Ty as her assistant. She then treats him really bad, and he quits. Sam tries to help a troubled teen.

Plot of this episode is not specified yet.
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Ty stays with Vandy after Dawnie tells her 2 friends (who are getting married) that they could stay with her. The only catch is that the groom, Matt was Jesse's old flame. They arrive and they throw a party for them. Jesse then admits to herself that she still have feeling for Matt. Gwen, the bride, tries on her dress and Jess gets jealous. While alterations her dress, Jesse tells Russell that she still loves Matt. Gwen then shows up and she wishes the best for them, But Jesse confronts her feelings to Matt. Matt being a guy he is, doesn't really solve anything. While having their some what official party for them in Vandy's bar, Jesse gets drunk and confronts her friends. She then says bad things about Matt and Gwen and they all leave Meanwhile in Vandy's home, Ty starts to control everything. He sets a mousetrap killing Vandy's house pet. Ty then tells Vandy sorry and buys him a hamster instead (they were sold out of mice) Jesse then apologies to Matt and Gwen and tells them she is

Dawnie tells Jesse that she is going to have a one night stand to lose her virginity. Ty moves in with Vandy, and Vandy hires Ty as a bartender; Dawnie's mother Barbara returns and slaps Ty on the face. Ty leaves and Dawnie reveals to her mother, Barbara, that she is still a virgin. One of Russell's co-worker, Steve hits on him and asks him for dinner which result into a one night stand; Sam helps Vince on a difficult case. Vince is jealous after his rival in court is charmed with Sam. Dawnie fails to have that one night stand; and Jules and Vandy attempt at a one night stand.

At Thanksgiving Russell tells Jesse and Dawnie that he will come out to his parents. Jesse, who tells everyone that she doesn't want to smoke anymore, visits Sam at work and invites Vince for Thanksgiving dinner. Russell's mother shows up and tells him that she and his father are getting a divorce. Russell then tries to come out to his father but fails. It's time for dinner and Ty, Vandy, and Jules arrives. Sam and Vince arrive and Vandy answers the door making him a bit crushed. But Vince quickly explains that he is her boss. He enters and they all (except for Sam, Jesse, and Dawnie, who is stressing on a perfect Thanksgiving dinner) watch the football game that is on. Ty and Jules get a little close making Dawnie a bit jealous. Sam tells Dawnie she forgot to add the stuffing. Dawnie then stuffs it violently and grabs the pan without the pot holder, burning her hands. Dawnie calms down. Russell, in private, tells his parents that he is gay and they just reply ""we knew"" which makes him

After the kiss, Dawnie confronts Ty that he is avoiding her because they had kissed. Jesse, and Russell are having coffee, and Jesse spots Coffee Boy. Jesse doesn't want to talk to him because he had asked her to read his transcript of his book which she found that it sucked. In a moment of weakness, Vince kisses Sam in work and leaves. Cliff wants to interview Russell for a story. Russell agrees and Cliff asks if he was gay. He says now and Dawnie walks in their apartment. He then lies and tells Cliff that Dawnie is his fiancée, and that they will have a party celebrating their love. They then invite him to their party in which he accepts, after rearranging his schedule; Ty then has a one night stand with a girl and tells Vandy that he loves Dawnie. At the party Coffee Boy tells Jesse that her opinion means so much to him and she tells him that his book sucks, making him leave; Sick of lying Russell tells Cliff that he is gay. Everyone leaves and Cliff reveals his true intentions with

Olivia visit Vince over their suit on divorce; Russell wants to do something different with Cliff so they decide to cook together. Ty asks Dawnie for this poetry book that they shared. Dawnie then remembers that she gave it away to Jesse. Sam and Vince decide to take things slow but end up in bed with each other. Vince gets a page from Olivia and tells her that he will talk to her later. He then hangs up and Olivia *69 his ass and Sam answers. Olivia gets angry when she found out that the person he is seeing is his assistant. Jesse notices that Sam is ultra happy around and she figures out. Ty then asks Jesse about the book but Jesse said she gave it away to Cliff. She asks Cliff but he tells her that he gave it away to a used book store; Olivia and Sam get stuck in an elevator with Olivia. They then have a little talk. Dawnie stalls Ty while Jesse, Vandy and she try to find the book. At the used book store Jesse bumps into Coffee Boy who also helps. Russell and Cliff's dinner plans f

Dawnie decides to lose her virginity saying it's her New Years Resolution (which is in two days.) Sam tells Vince that they can be a normal couple in Russell's soap bash party. Russell is devastated when Cliff tells him that they can't spend the New Year together because a trip in L.A. Jesse tells Coffee Boy that she wants to spend a night in for just the two of them as the year comes to an end but Coffee Boy says that his resolution was to finish his book and couldn't spend time with her, which makes her angry. Dawnie tells Russell that she wants to lose her virginity to Russell's soap character in ""Hamton's Shore"" and not him. He then disagrees and attends the party with the rest. Dawnie is sick of staying home and heads for the party where she meets and incredible guy named Holt which turns out to be a porn star, as ""Holt the Bolt"" in which Vandy and Ty recognized in the men's bathroom while peeing (""his woody""!) Coffee Boy shows up at the party and talks to Jesse. He tells her that

The Morning After, Russell who is super delighted barge into Dawnie's room. He wants to talk about last night, only to find out that she is not alone. Vandy then pops up and Russell is puzzled. Russell then calls Jesse, who is devastated to find that she is alone. But Coffee Boy pops up and she hangs up on Russell. Russell being super hyped rushes to Jesse's apartment and tells her. She is shocked and Russell tells her not to tell anyone but she tells Coffee Boy after Russell left. As a tradition everyone heads over Dawnie and Russell's place to write their resolutions. Sam wonders about the commotion and Jesse proceeds to tell Sam but is interrupted by Dawnie. They all proceed to leave and Ty wants to talk to Vandy. He then punches him in his face after finding his lucky scarf that he gave to him on New Years night. He tells him that he slept with Dawnie and didn't tell him. Nowhere to go Ty hides out in Vandy's storage room. The gang all returns to Vandy's bar and Vandy finds him in

Vandy and Dawnie feel awkward around each other; back at work everyone knows that Sam and Vince are a couple which jeopardize Vince's job. Rumors speculate and Vince gets a call from the ""big cheese"" and tells him to stay away from Sam. Vince then tells Sam that he wants to keep their personal and professional life separate which upsets Sam a bit. Dawnie gets a new teacher and challenges her on her thesis. She then proceeds to write a whole new report; Jesse feels weird around Coffee Boy after telling him ""I love you"". Vandy and Dawnie want to talk to everyone about their relationship but didn't realize that everyone has a problem of their own. Jesse being uptight invites Russell to Coffee Boy and her dinner. Russell then leaves after Coffee Boy asked him to. Coffee Boy confronts Jesse on being weird for the past days. She then replies ""You never say 'I Love you back'"". Sam then breaks up with Vince and Vince gets heart broken. He then clears the rumor that they are dating. Jesse feeli

Jesse meets Angelina (Played by the talented Lori Heuring!), Coffee Boy's Ex. She feels threatened after they start to get close. The big cheese gives Vince lower cases which upsets him. Dawnie and Vandy try to talk to everyone but they are still suffering from new problems and no one wants to talk to them. Gothic Bill, Vandy's roommate dies after Vandy returned home. Ty returns to Vandy's place and starts to forgive him a bit. Ty then stumbles on Gothic Bill's will. Dawnie's teacher then asks her to turn in a sample of her thesis and she says she likes the new thesis about death and all. Dawnie then works extra hard on her thesis as the deadline comes near. Russell while checking his email crashes Dawnie's computer and as a computer technician to fix it. He then fixes it and recovers Russell's email from Cliff saying that he wants to break up with him. The computer then crashes again. Ty doing Gothic Bill's wish gets his ashes but drops it by accident. He returns to Vandy's place and