Danny Burton (Chris D'Elia) is a 30-ish carefree single guy who has watched most of his friends move on to serious relationships. When his last remaining friend Shannon moves out to get married, Danny searches for a new roommate. A promising candidate is Justin (Brent Morin), the owner of the Black Eyes Bar in Detroit. Justin and his friends - the nerdy Burski (Rick Glassman), oddball Shelly (Ron Funches), and recently out-of-the-closet gay guy Brett (David Fynn) - all have certain qualities that make them appear "undateable". While Danny himself has good luck getting women into bed, he is unable or unwilling to form a lasting commitment with any of them. Danny's attractive sister, Leslie (Bianca Kajlich), has similar fears about being undateable, having the "baggage" of being a mid-30's divorcee.
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