Trama

Josh's girlfriend wants to get married. Molly's boyfriend is married. Josh and Molly fly to the wedding in Chicago together and pretend to be engaged to make their parents happy. Comedy follows...does romance?

On a flight home to Chicago for a family wedding, childhood friends Josh and Molly innocently agree to fake a engagement to make Josh's dying father happy. Things quickly get out of hand with their two boisterous families, and a series of events causes them to pretend to be a couple and start to plan a phony wedding.—Anonymous

Molly Mahoney (Aubrey Dollar) is flying home to Chicago for her mom's wedding, bringing a "Mystery Man" with her, but when she discovers that he has a Mystery Wife, she dumps him at the curbside check-in and ends up crying on the shoulder of childhood friend Josh Shiffman (Shane McRae), who is flying home for the same wedding. Emotionally drained, Molly passes out in Josh's arms just as he gets a phone call from his parents. Josh learns that his father is dying and his only regret is that he will not get to meet his son's future wife. Desperate to fulfill his dad's final wish, Josh claims he has already met that woman: close family friend Molly Mahoney. When Josh sheepishly confesses his ruse in mid-flight, Molly is furious and makes him promise to right the wrong the moment they land. But when they land--it's too late. Word has leaked out and they are swarmed at the airport by BOTH FAMILIES with well wishes and congratulatory banners. Molly's family is delighted that her "Mystery Man" turns out to be Josh, and Josh's dad is thrilled that his playboy son is finally settling down with a nice girl they've known all their lives. Josh convinces Molly to play fiancée by using a deadly combination: her Catholic guilt and his playboy charm. But as they plan their phony wedding, they start to fall in love for real. This turns their dating lives, and family's interactions, hilariously upside-down tugging on every heartstring in the process.

In Los Angeles, Josh is kissing a beautiful girl who is typical of his dates. He protests that he will be late for his flight to the Chicago wedding of his best friend Sean's mother, and then he sees the girl has given him a pile of magazines to read on the plane, all of them about preparing for weddings.

Also in Los Angeles, maid of honor Molly, who is the last single girl in an Irish Catholic family, tries on her bridesmaid dress for her friends. Then she gets a call from boyfriend Lance (her ring tone is "Here Come the Bride" and it is never changed even when the wedding is over). Lance shows up to pick her up playing loud music. Molly is also going to Chicago for the same wedding, and she intends for the family to meet Lance, who is a loser in a band. But at the airport, Molly and Lance get in a fight because he cheated on her with his wife. Molly takes her luggage with her and cries in the restroom, where a sympathetic flight attendant listens to her story and gives her something to make her feel better.

Josh's flight is delayed and as he waits in a bar, he wastes no time in picking up yet another woman, Risa. But then Molly walks into the bar behaving strangely. Molly's brother Sean, taking care of baby Zach, calls Josh. Josh then has a conversation with his old friend Molly, and as he is trying to help her, his mother Frida calls, angry. Josh explains his flight was delayed and his mom says he could have called her. Josh's dad Max joins the telephone conversation and says he didn't want to say it over the phone, but he has to. The doctor says his cancer is terminal. When he says he wishes he could have lived to see Josh get married, Josh decides to tell Max he is engaged and that he knows the woman. Molly reluctantly agrees to go along with the deception since Josh just told Max, and she passes out so Josh has to put her on the plane.

Thinking they can get to their destination without fanfare, Josh and Molly get off the plane in Chicago. Numerous people from both families are there to welcome them, and the happy couple receives congratulations.

Josh and Molly have to pretend as they visit with both families. A little girl asks Molly what the children will be. The girl has to explain Jewish children are normally raised Jewish by their mothers, and she knows that Josh is Jewish but Molly isn't. The question isn't really answered.

Josh and Molly are offered the guest room, but they say they would prefer a hotel. But Josh's parents come up with another solution: a nice apartment that is used for storage. So Josh and Molly go there and spend the night, with Molly taking the bed and Josh taking the sofa.

The next morning Josh gets up early to help get ready for the wedding. Max gives Josh his grandmother's ring to give to Molly.

Sean is furious his best friend didn't tell him about being engaged to Molly. Josh and Molly jog over to visit Sean and wife Carla and explain the situation. Molly is absolutely exhausted because she is not used to so much exercise. Molly ends up spending a lot of time with Carla.

Josh and Molly also have a meal with his parents, Molly's mother Doreen who is the bride, and Al who is the groom.

Just before the wedding, Molly's friends wonder how a man like Josh ended up with her, and they conclude Molly must be pregnant. Then one of the girls looks out and sees Josh giving Molly the ring. She is reluctant to wear it, but Josh agrees and when he drops the ring, he has to kneel down to pick it up. The bridesmaids are delighted.

Giselle, who is gorgeous, used to be Josh's girlfriend and she is happy to see him. He is happy to see her and of course he would like to get back together. As he is about to explain his situation privately, one of the relatives comes up and hugs Josh and spills the beans about Molly.

Because they are engaged, it is decided Josh and Molly will walk down the aisle together.

After the reception, Josh and Molly go back to their apartment and after Josh is already undressed, Molly is too drunk to take off her dress without assistance. Josh helps her, and then she ends up in bed with Josh, but nothing happens.

It's just as well they ended up in bed together, because Frida shows up and lets herself into the apartment. She explains to Josh that she needs his help at The Framery, the family business which puts art work in frames. In fact, although Josh never explains his job situation, Frida wants him to stay and help out for longer. Molly's job situation is also never explained, although that would provide her with an excuse to go back home. Nevertheless, they both agree to stay and both of them help out at the business. Josh was taught well by his father, because he does a good job making deals.

Doreen's dress was rented so she and friends take it back. When the overly enthusiastic employees learn Molly is engaged, Molly is told she just has to try on dresses.

Josh meets Giselle at the Rockit bar, and Giselle is very understanding when Josh explains. She is willing to be a "friend with benefits".

Molly and Carla have a spa day.

Max and Frida look at the 100-year-old Crystal Ballroom as a possible wedding venue. Frida sees Josh and Giselle kissing and is horrified, but distracts Max and the hotel employee.

Max and Josh have a conversation that makes him realize that he is happy with Molly and there would be no one better.

Molly is secretly having her own good times without Josh, and she dresses up and looks even prettier than she did at the wedding. She doesn't actually know where Carla is taking her, and Carla realizes she has to go back to the apartment to get something she forgot. It is a surprise bridal shower. Asked when they first slept together, Molly says she and Josh were young children, since they were friends back then (or at least she was the annoying little sister). She still won't explain how she and Josh ended up together. One of Molly's presents is a naughty black outfit, which she puts on back at the apartment while she and Josh finally have sex.

Josh and Molly go through the motions, marking possible wedding gifts at a department store. Giselle is there, and she and Molly appear to get along, but from a distance, Molly seems jealous.

Josh and Molly and both sets of parents try out cakes and other food. Max eats spicy food despite Frida telling him not to. Molly gets upset, gives back the ring, and gets in a cab. Josh gets in another cab. Max gets sick and has to go to the hospital, where Frida demands the best of care for her husband who just had a heart attack. Josh is with Giselle breaking up with her when he finds out, and he brings her, and Frida can no longer keep quiet about Josh's cheating. Giselle's presence makes the family angry. Sean shows up and hits Josh for sleeping with his sister and then doing this. Molly finally comes clean about the deception, while Max is told he just had heartburn.

Josh kneels and gives Molly the ring once again, saying she is the best person he could be with. Max returns to the family.