A young couple, Ben and Sara, laugh at the stadium music (Ben's choice) still playing in the background after finishing up some quality one-on-one time; Ben claims it makes him feel like he's "winning." Their post-coital conversation takes a surprising turn when Ben asks Sara how her date that night went. Apparently, these two aren't a couple at all.
Sara reveals that her date with Rich went well, besides the fact that he asked her to pay the bill at dinner. Ben notes that this should be a deal breaker, but Sara is willing to lower her standards; she didn't have the time to date during med school, and at 28, she doesn't have the luxury of picking apart people like Ben does. Ben tries to defend himself; he doesn't pick apart girls. But Sara has a point; his last three breakups were for completely menial reasons.
Ben then asks Sara to go with him to his sister's wedding; he already RSVP'd plus one, and his family always gives him heat for not having a girlfriend. Sara refuses to go; that's a girlfriend's job. And she is definitely not his girlfriend.
The next night, at a bar, Ben's breaks down a recent date to his buddies Aaron and Fitz. Apparently, since his date didn't like "Caddyshack," Ben wasn't into her. Their friend Riley the bartender walks in wearing a bee suit, explaining that she's dating a congressman (as if that's enough of an explanation). In Ben's position, Riley would have slept with her date anyways... but then again, she's wearing a bee suit.
Softie Aaron gives his two cents, claiming that Ben just hasn't found his Katie yet. Katie is a girl that Aaron's been dating for three months (he prefers to say 13 weeks.) It hasn't been long; but he knows she's the one, and he is going to make a bold move and ask her to move in with him.
Ben walks in on Aaron with a golf coach; apparently, Aaron hired him in his ongoing quest to beat Ben at video golf. Really, it's no expense to Aaron, who became a millionaire after selling a nanotech start-up to Google for 12 million dollars. Ben confides in Aaron about his and Sara's relationship. An overeager Aaron wants to know the details - are they in love? Ben explains the nature of their "friends with benefits" relationship, but Aaron can't seem to wrap his head around it.
Ben decides to face the music and let his sister know that he's not bringing anyone to the wedding. But hearing his sister laugh at the possibility of Ben even having a girl to bring makes him change his game plan. He tells her that he is bringing someone; in fact, he has a girlfriend. And she is his soul mate. Ben's family is thrilled to hear the news, but now Ben has a serious situation on his hands. Ben and Sara brainstorm dates for Ben to bring to the wedding. Sara suggests a past girl he was involved with, Dakota, and Ben decides to go for it since he can't remember her deal-breaking flaw.
On his date with Dakota, Ben can't figure out what was wrong with her despite his efforts. But on Sara's second date with Rich, things crash and burn when Rich takes Sara to a swingers club.
Meanwhile, Aaron shows up at Katie's doorstep with a horse for their three-month anniversary. He's alarmed to find Katie with another man, "Dirty Mike." Katie admits that Aaron is the kind of guy she should be with, but he's just too good to her. Later at the bar, Riley comforts Aaron. Aaron admits that he wishes he could just have casual sex, but he can't seem to figure it out. At this, Riley takes control and grabs Aaron's face and kisses him.
Ben finally figures out Dakota's flaw: she's a terrible kisser. No really, she kisses like a thirsty bird or a hobo cleaning out a margarine container. When Ben is honest with Dakota about her kissing, Dakota counters - he's not perfect either. He has a Velcro wallet, talks with his mouth full and his ears are crooked.
Aaron and Riley are back at Riley's apartment, going at it. Despite Aaron's attempt to talk things out, Riley shuts him up when she tells him to take her top off. Meanwhile, Ben and Sara rendezvous at the steps of Ben's apartment. Sara admits that she could be a little choosier, while Ben admits that he could be a little less choosey. At least in the meantime, they have each other.