"This is gonna surprise you, but I used to be considered something of a nerd." - Stuart
True to the nickname he's earned, "the creepy caller," Stuart unsuccessfully hits on a woman in yoga class. Jessica encourages him to go for someone who's actually interested - like Annie, a juice bar attendant who's outrageously flirty with him. While asking her out, Stuart falls into a cooler, but Annie obliges with her phone number anyway.
Stuart schools Rory on the texting etiquette of dating, including deliberately delaying your response. He's surprised when Annie replies right away and accepts his invite to Vouloir. They meet at the new restaurant and Stuart is horrified to find an exorbitant menu. His fears are realized when Annie proves to have expensive tastes. Stuart chases the waiter down several times, asking him to claim the more expensive items are currently unavailable. Despite the bill, both Annie and Stuart have a good time and set another date to play mini-golf the following weekend.