Kim and Dwight go out to a dinner where she schools him on the proper way to behave on a date with a girl. Not to be outdone, Dwight gives Kim some advice of his own on what it's like to be the founder of a start-up. A new love triangle arises when Hermione goes out on a date with Jay where the chemistry that was missing on his date with Sarah is plentiful. Meanwhile, Ben seeks Hermione's approval to take Sarah out on a date. David vents his frustrations about struggling to make ends meet while trying to launch his start-up, Goal Sponsors, and he decides to ask Sarah for a loan to ease the burden, but will she say yes? And when David brings his friends together for a night of line dancing, Sarah finds out about Jay's date with Hermione, which puts her in an emotional tailspin.

Much to Hermione's chagrin, Ben takes Sarah out on a date to the fair. Dwight visits with his parents where they discuss the unpredictable future of Carsabi. And Hermione celebrates her birthday in true Villa style filled with friends and even potential investors. But when she decides to chase people around with a less than appropriate sex toy, Ben becomes worried that they may have just lost $500k in potential investments.