Loser Annie (Wiig) is anything but successful. She leaves dubious lovers undignified (mostly over the fence), she's terrorized by customers at work (and she is, so the threat of being fired hangs over her permanently). The only bright spot in her life is her friend Lillian (Maya Rudolph). She's just announced she's getting married, and Annie, being her best friend, understandably promises to help her with the wedding preparations. She's all the more eager to do her bit as four of Lillian's other friends, including the beautiful, wealthy and smart Helen (Rose Byrne), want to contribute. And so Annie helps and plans like hell, and as is often the case in her tragic reality, what she touches fails at best, or ends up with an arrest, food poisoning, a hideous scene involving a chocolate fountain, or sex with a traffic cop. Take your pick, whichever is worst. Maybe it's that Lillian is running out of patience with her (slowly ex) friend.
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