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Emmaline is convinced that she is ready to settle down. She is 24. Has the man of her dreams, the job of her dreams (well at least she’s got her foot in the door of the right industry) and the best friends a girl could ask for. She’s leading the independent in life in Somerville, MA, working in Boston and going out, enjoying the city life. However, her fantasy world comes crashing down the night before she leaves on her first business trip when her long time boyfriend, Frederick, breaks up with her. She is sobbing, her life is over. She will never get married. She will never get a dog. She is nothing. She is devastated to be single again (although she has rarely been single her whole life).

Everyone has advice for her on the "Right" thing to do. Her sister, Abigail, tells Em she needs a white collar man, a rich, wealthy, smart man who wears the right clothes, knows the right people and says the right things (with the correct pronunciation). Her best friends think she needs to forget about Fred and find the next best thing...they all hated him anyways and they aren't afraid to tell her now that they're broken up.

Em decides she's going to meet the man of her dreams & marry by the end of the year if its the last thing she does. She never wants to feel this miserable again and she will do anything to get her man because she strongly believes that is what will make her whole. After all, her clock is ticking, and she needs to meet her goal of husband, house, dog and kids.

Em begins trying to meet men, from dating pools to dating games, Buddhism, AA, blind dates, art therapy; Em tries everything to meet a man. Just when she is ready to write off all men, realizing she’s not going to get married by the end of the year; in fact, she may be swearing off men forever, Em begins to really notice Ethan, the office guy. She decides she can’t give up on trying to get her man and goes after this one last time.

Ethan seems like the perfect guy despite his working class, poorer than usual image. After dating Ethan for a while, it seems like Em is going to get her “happily ever after” after all. Just when she thinks she’s going go to be happy, Fred comes back – now that she doesn’t have any interest in him and ruins things for her and Ethan. Fred tells her that Ethan is not who he says he is. Em confronts Ethan who confirms it and she is humiliated at office by him. She begins to doubt her faith in Ethan but her idea of who he might be is different from the truth, but she of course believes the worst.

Em reaffirms what she thought in the beginning – that she’s better off on her own. After all the dates and drama with Ethan, she realizes that she doesn’t need anyone but herself. She realizes that true contentment actually comes from within.

Finally, Ethan finds a way to let Em know who he really is. She realizes that her true goal is to find independence and be happy with herself whether or not that means she ends up with Ethan. So what will happen? Does Em find true love and happiness with Ethan or go back to Fred? Can she find happiness and be alone? Find out what happens in this rollercoaster adventure of one woman’s search for herself through the dating game and life in the city.