Annie, Cassie and a few other girls celebrate Liz's bachelorette party in a limousine. Pregnant Annie pops out of the moon roof to yell to New York City. Back inside the limo, Annie gives Liz her present - a vibrator. After a very drunk Liz nearly passes out in the limo, her friends carry her back to her hotel room while Annie retouches her makeup to go out with Cassie. But Cassie hails a cab, trying to ditch Annie. Whenever they go out, Annie gets all the attention for being pregnant and Cassie feels invisible. It's because Annie has a great story - she's carrying the baby as a surrogate for her sister. Cassie laments that she doesn't have a good story to catch guys' attention. Annie promises to keep her mouth shut and they head off to a bar.
At the bar, Annie and Cassie spot a cute guy, Jordan, scribbling on a napkin. He explains that he's writing down an idea before he forgets it because he's working on a novel. When Jordan starts asking Annie about her baby, Cassie starts to panic and blurts out that she's a virgin, which Jordan finds kinda sweet. Cassie says good night to Annie, who leaves. Later, Cassie and Jordan make out at Cassie's apartment. She drops a "Battlestar Galactica" reference, which Jordan finds hot because he's also a huge fan. Jordan thinks maybe they should slow down because he thinks Cassie's a virgin, but she insists she's ready. In the end, Jordan decides they should slow it down, pecks Cassie on the cheek and leaves, promising to call.
Three days later at work (at a restaurant), Cassie complains to Annie that Jordan still hasn't called. Annie wonders why Cassie made up her "virgin" story. Cassie worries that she really screwed things up after meeting the perfect guy. Annie tells her not to worry; Jordan's probably not even freaked out. Meanwhile, Jordan plays football in the park with his buddies, freaked out that Cassie's a virgin. It's a huge responsibility to be someone's first! He doesn't know what to do, because he really likes Cassie.
Back at the restaurant, Cassie's other coworkers tell her that Jordan isn't going to have sex with her because no guy wants to be the first. Jordan's friends urge him to have sex with Cassie because encountering a hot 20-something virgin in this day and age is like finding a unicorn. It's time to "bang the unicorn"! Just then, Cassie texts Jordan. He texts back that he's sorry he hasn't called, and he wants to get together later to talk. Cassie thinks Jordan is going to let her down gently because he thinks she's a virgin. Annie suggests telling Jordan the truth; he'll understand. But Cassie fears he'll hate her because she's a crazy liar. Annie tells her that's just a chance she'll have to take.
Jordan and Cassie sit on a park bench. Jordan apologizes for the other night. Cassie starts to tell the truth, but he stops her. He's hired a horse-drawn carriage, and the guy's early. Jordan wants to make the first time really special. In the carriage, Cassie confesses she's not a virgin. She lied because she thought she needed a good story to hook a guy. Cassie points to the attention Annie always gets, and Jordan explains that guys have to be nice to pregnant girls or risk looking like a douche. Cassie realizes that Annie was her wingman, and she blew it, then guesses all of this will go into Jordan's novel. Now it's Jordan's turn to confess - he's not writing a novel, he just said that to sound interesting. Cassie declares they're perfect for each other because they're both liars and Battlestar fans. They agree to a fresh start.
In San Francisco, Carter arrives at the law firm where he works as an accountant; his officemate Kell says the boss wants to see him. The boss explains that the firm is implementing an automated timekeeping system, and as a result, Carter's being laid off. Carter calls his buddy Judd from the men's room to tell him about being fired. He's freaking out because he's getting married in a month and just moved into an expensive apartment with his fiancee. In the middle of the conversation, Judd, who's standing over a bridge, drops his phone in the water. Just then, Carter hears a flush, and Kell emerges from a nearby stall. Kell gives Carter a pep talk; his fiancee Liz will understand. In the hallway, one of their coworkers tells Kell the boss is looking for him too. Realizing he's next to be fired, Kell loses his composure.
From outside his apartment, Carter hears his fiancee, Liz, moaning wildly. Certain she's cheating on him, Carter resolutely climbs the stairs to their apartment and throws open the bedroom door to find Liz alone. When Carter admits he thought she was with someone because she was moaning so loudly, Liz explains that Annie gave her the "Maserati of vibrators" as a bachelorette party joke, but it's no joke. Carter wonders how he's only getting a lame fishing trip for his bachelor party and she got sex toys in Manhattan. Maybe he should cancel the trip to save money?
Carter starts to tell Liz about losing his job when she interrupts to declare that she thinks she just had her first orgasm. When Carter wonders if she's been faking the whole time, Liz assures him that she hasn't been, she's just now realizing that what she thought was an orgasm before might not have been one. Carter's clearly bothered, and Liz wonders if she shouldn't have told him. Although he maintains they should be able to tell each other anything, he punts on telling Liz about getting laid off.
Carter and Kell jog on the beach. Carter complains: he's been replaced by a machine both at work and in bed! How's he supposed to compete with the "Maserati of vibrators"? Kell says that devices like that should be the first thing to go when two people move in together, just like a guy's porn has to go. That way, the bitterly divorced Kell fumes, when you get divorced, you've got no woman and no porn... and now, no job. Kell reassures Carter that Liz isn't going to leave him just because he doesn't have a job. Carter declares that while he doesn't have a job, his job will be to become as good in bed as the Maserati of vibrators. Step one: knowing your competition.
Carter and Kell go to a sex shop to check out the vibrator. Intimidated by its many features, they wonder how they're supposed to compete if sex toys keep getting faster and more sophisticated. The saleswoman advises them to get faster and more sophisticated. Carter leaves, declaring that he will. Kell approaches the saleswoman to ask if it's fun working there. She tells him that she has a boyfriend, so he explains that he's actually looking for a job. Back at home, Carter studies Liz's vibrator. To his dismay, he discovers yet another feature - heat! The next morning, Carter does his best to give Liz an orgasm. She stops him, saying she has to get to work. When he asks what he can do, Liz suggests using the Maserati. Carter laments that he's the fluffer.
Carter meets with a headhunter but flubs the interview because he's lisping. He tries to explain that he may have sprained his tongue. Later that night, Carter and Kell walk down the street eating slices of pizza. Kell thinks they should give the injury a name, like "Carpal Tongal." Carter's stressed out because Liz is having the best sex of her life without him. Kell points out that for women, communication is key.
Later, at home, Carter and Liz watch TV. Amidst an interview with Jennifer Love Hewitt about breaking up with her latest boyfriend, which Liz is enjoying, Carter switches to a porn movie. Liz is a little shocked, but when Carter claims it helps him get in the mood, she decides she's okay with it. Then she asks Carter if she should pull out her Maserati. Carter gives up, saying why not. Later, in a burst of passion, Liz cries out that she loves Carter. Carter responds by blurting out that he lost his job. Liz turns off the Maserati, to ask why he didn't say something sooner. Carter feels like he's supposed to support her - he's the guy. Liz reassures Carter that she has faith in him, and he's going to find another job. Carter admits that he does have a temp job - to be better in bed than the damn Maserati!
On the way to LAX, Judd and his buddy Bowman sing an ad-libbed song about going fishing, as Judd's wife Colleen drives them to the airport. Colleen wonders if they need to establish ground rules for the bachelor party. Judd insists it's just going to be a lame fishing trip with no strippers. When Bowman wonders why they're flying cross-country for a G-rated bachelor party, Judd reminds him that Carter lost his job and needs cheering up. Suddenly, Judd freaks out and tells Colleen to pull over to the curb, pointing to Jennifer Love Hewitt. She's the first and only person on his Celebrity Exemption List, the list of famous people you can sleep with if given the chance and it doesn't count as cheating. Colleen encourages Judd to run after her because she doesn't think he can make it happen. Judd doesn't think so either.
As they board the plane, Bowman comments that the problem is they're going to Miami, where there will be hot babes everywhere except on a boat with four dudes. Seeing Jennifer Love Hewitt sitting in first class, Judd and Bowman gape as the flight attendant encourages them to find their seats. The guys discuss the many challenges Judd faces, including the class difference and the fact that Jennifer Love Hewitt has a boyfriend, a professional hockey player who puts guys in the hospital. If Judd winds up beaten to a pulp with a hockey stick, he'll have done better with her than anyone could have imagined.
Bowman wonders if the whole premise of the list is that it's never going to happen. Judd knows it's a long shot, but he's got to try this. He knows Jennifer Love Hewitt likes tattoos, and he's a tattoo artist; so he'll sketch something for her - on a barf bag. Just then a woman with a crying baby approaches their row. Later, the baby's still crying. The woman apologizes; the baby just wants his mother, who's in first class. Turbulence knocks a drink onto Judd's sketch, so he gives up. There's no way he's ever getting into first class. Just then, the baby's mother shows up, offering to trade seats with Bowman. She's been sitting next to Jennifer Love Hewitt, who kept wondering why the crying baby's mother didn't do something. Now she can't go back and face her. Bowman tells Judd to take the first class seat.
Judd heads for first class and sits next to Jennifer, who sympathizes with the baby. Turbulence makes her feel like crying too. Her boyfriend used to hold her hand and of course, now that they've broken up, she's on the flight from hell. She's done with athletes! When she asks if Judd's an athlete, he points to his tattoos, indicating that he's a tattoo artist. Jennifer loves tattoos! After another jolt, he offers to let her hold his hand. Jennifer double checks that he's married, then tentatively takes his hand, asking if he's ever cheated on his wife. He swears he hasn't. The secret to staying faithful is love and trust for his wife. Then Judd mentions the Celebrity Exemption List, admitting she's first on his list. Jennifer doesn't have an exemption list, but she does have a to-do list, as in places she'd like to do it. And first on her list is on an airplane.
Judd bolts out of his seat, saying he left something back in coach, where both the mother and nanny are sleeping against Bowman, who holds the baby. Bowman gives Judd a condom from his wallet. When Judd worries Colleen may not understand, Bowman reminds that Colleen said she was game, which means he finally gets a shot at Colleen. The flight attendant interrupts to announce the Captain has turned off the fasten seat belt sign and they're now free to move about the cabin.
Judd returns to his seat to tell Jennifer he's heading to the lavatory. She follows a minute later. Once inside, Judd and Jennifer fumble awkwardly and Judd drops the condom. Sudden turbulence throws Jennifer into Judd just as the flight attendant announces that everyone needs to return to their seats. Judd remarks that never having sex with the first and only person on his list beats bad sex with that person. Hearing that she's the only one on his list, Jennifer offers a quickie. But Judd can't go through with it. He doesn't want to cheat on his wife, even though it's not cheating. Now Jennifer doesn't want to sleep with Judd, she wants to marry him! She asks if she can lie and say they had sex because it will drive her ex crazy.
On the ground in Miami, Judd hugs Jennifer goodbye. She takes his tattoo sketch, promising she's going to have him do the tattoo. Afterwards, Judd calls Colleen to tell her about turning down Jennifer because he loves Colleen. Colleen tells Judd that's too bad because she hooked up with Johnny Depp at a party. Back in New York, Annie chats with a cute guy at the bar, telling him her surrogacy story. Cassie leans over and tells the guy that she's seeing someone, and he leaves. Annie realizes that now she's Cassie's wingman.
In San Francisco, Carter and Kell's former boss brings some pink fuzzy handcuffs to the cashier at the sex shop. Kell puts down the paper he's reading to reveal that he's now the cashier. The boss offers Kell his job back if he promises never to speak of this. Kell doesn't want his old job back, but he does encourage his ex-boss to buy less cute handcuffs. The saleswoman yells at Kell from across the store to stop yapping and make the sale. In Miami, Judd talks to Colleen from the boat dock, begging her to admit she was joking about Johnny Depp.