Original air date: 08/05/2011 Runtime: 21:40 min. Sara and Ben are good friends who often find themselves in each other’s beds after one or both has a bad date, sometimes on the same night as said bad date. They are both actively involved in the dating scene (Sara much more intently than Ben), but still haven't found the right person. Sara is currently struggling with whether or not to give a guy who made her pay for dinner on their first date another chance, and Ben is desperate to find a date for his sister’s wedding lest he look like a loser.
Original air date: 08/05/2011 Runtime: 21:20 min. Sara surprises Ben by asking if they can put their casual-sex thing on hold for a while. She’s met a great new guy who is real boyfriend material, and wants to give him her undivided attention. Meanwhile, Ben attempts to close the deal with an out-of-town guest, and Aaron considers his next move after his hook-up with Riley.
Original air date: 08/12/2011 Runtime: 21:20 min. When Aaron becomes depressed over a former college crush getting engaged, Ben and Fitz decide to take him out for a night on the town. They end up arguing over a girl. Meanwhile, Riley is convinced that Sara doesn’t want to hang out with her because she looks down on her. Hoping to prove that she can keep up with Riley’s wild lifestyle, Sara hesitantly agrees to accompany her to a friend’s party.
Original air date: 08/12/2011 Runtime: 21:20 min. Ben begins dating a former girlfriend, and reaps the benefits of her short-term memory loss. Fitz’s lesbian mother comes for a visit, and he takes it upon himself to find her a new girlfriend. Riley dates a man who has a creepy obsession with breasts.
Original air date: 08/19/2011 Runtime: 21:17 min. Sara struggles to get off the booty-call track and onto the relationship track with a paramedic she met at the hospital. Meanwhile, Ben works toward the opposite end with a girl he met over the weekend. Fitz, humiliated and frustrated by Aaron's extravagant gift on their "roommate-aversary," shuns Aaron’s courtside tickets, and instead has them sit with the masses to prove a point.
Original air date: 08/19/2011 Runtime: 20:23 min. In an attempt to avoid a date with a nerdy co-worker, Sarah asks Aaron to bid on her at a charity bachelorette auction. Meanwhile, Ben accidentally uses a suggestive phrase with a co-worker, getting himself accused of sexual harassment. Fitz thinks he's in the clear to spend one last night as a single man before committing to a monogamous relationship, but finds out his girlfriend feels differently, and scrambles to cover up incriminating photos from his wild night.
Original air date: 08/26/2011 Runtime: 21:18 min. The gang plans a trip to New Orleans for Mardi Gras. After an argument with her sister over a family heirloom, Sara is reluctant to stay with her family in Louisiana for her sister’s baby shower and Mardi Gras, but her friends convince her that they will help her through the weekend. Meanwhile, after one too many drinks at Mardi Gras, Aaron finally musters up the courage to tell Riley how he really feels.
Original air date: 08/26/2011 Runtime: 21:12 min. Aaron discovers that a girl he mentored in junior high has become a successful porn star, and feels he influenced her poorly. At the hospital, a doctor who Sara admires falls for Riley, and bribes Sara with highly coveted surgeries in exchange for her help with inside information. Fitz and Ben visit a friend in the hospital after a sporting accident leaves him unconscious, and encounter his attractive girlfriend… whom they both fall for.
Original air date: 09/02/2011 Runtime: 21:18 min. While dating a man who is blind, Sara finds herself constantly craving compliments about her attractiveness. Meanwhile, the new girl Ben is dating always wears a very large brimmed hat causing him to panic. Elsewhere, Aaron dates an older woman who is only interested in his body, while Fitz makes a real connection with her daughter.
Original air date: 09/02/2011 Runtime: 21:15 min. When Sara accidentally gets involved with her ex-boyfriend Joe, she begins losing a sense of who she really is. Ben tries to help and stages an intervention only to end up doing the same thing with his ex-girlfriend. Fitz attempts to keep Sara and Ben sane, while Riley is shocked by Aaron’s actions when he tries to impress a woman with his money.
Original air date: 09/09/2011 Runtime: 21:20 min. Ben asks Aaron to invest in a macaroni & cheese food truck idea, but the business proves to be a problematic investment. Elsewhere, Sara dates a cute journalist on antidepressants, which makes physical contact very challenging. And Riley helps Fitz become number one on Chicago’s most “doable” bachelor list after researching the current number one bachelor.
Original air date: 09/09/2011 Runtime: 21:19 min. Ben finds that his life is in a slump and he misses the relationship he once had with Sara. When Sara’s boyfriend questions her history with Ben, she reluctantly lies to him, only to make matters worse. Meanwhile, while playing a drinking game, Riley meets a man and quickly falls in love, but her joy turn to sadness when she learns he might be dying.
Original air date: 09/16/2011 Runtime: 21:20 min. Sara is asked out by a guy she met while playing tennis, and he asks her if she has a friend for his female tennis partner. Ben is up for a double date, but Sara is worried that it could be awkward, considering that she’s still sleeping with Ben. Meanwhile, Riley dates a guy who believes in full disclosure, meaning that he’s brutally honest with everyone.