A man walks into a bar and talks to the pretty girl he has been introduced to through a mutual friend. He thinks the conversation goes relatively well. She thinks talking to him is "like pulling teeth" and wonders why he doesn't talk more. A man walks into a bar and plays flip cup with his new kickball team. He is terrible at flip cup and things go relatively poorly, but at least the pretty girl is there as well since she's the captain. She thinks the new guy shouldn't have told her how to set the lineup one week into the season and wonders why he talks so much. A man walks into a bar having walked on the Ocean City beach the night before. He still talks too much, or too little, but things are going well again. The night before the pretty girl asked him on the beach "Are you ever going to kiss me?" He did.
After a long period of dating, one which some might categorize as too long, Addy told Rachel they would be going to brunch together to celebrate Valentine's Day. Generally aware that they had been dating for the aforementioned "too" long a time period and explicitly tipped off by Addy's initiative in making a reservation; Rachel knew what was happening the moment she arrived in the lobby of the apartment building to find a friend standing there with an envelope. Fortunately, she was more surprised at the events that followed. The envelope contained a poem from Addy that was a clue to go to a place in DC that was of importance to Addy and Rachel's relationship. She traveled to the zoo, the site of their first date, where another friend held another envelope with a letter and clue. She continued on to the first meeting place, first place of saying "I love you", and the mall (kickball!) before returning to the apartment. It was there Addy proposed and Rachel realized she was not too upset about being stood up for Valentine's Day brunch.