After weeks of working in Washington D.C. together (and what Jake viewed as flirting and Lindsy viewed as being friendly) Jake finally worked up the courage to tell Lindsy that he wanted to be more than friends. During a night of fun with friends and colleagues, Jake walked up to Lindsy and told her how he felt. In return he received a stare that lasted for 45 minutes (or at least that's how it felt). Determining that the feelings were not mutual, Jake departed with friends to another spot, while Lindsy remained at the bar where Jake spilled his guts. Later, while Jake moaned about how he was never going to take chances like that again, he received a text from Lindsy, asking him where he was. After 30 to 75 minutes of processing (her minimum requirement when faced with feelings), Lindsy concluded that she was willing to take a chance on her cute coworker and see where things went. She met him at the Madhatter where he bought her a drink and they danced the night away. A couple weeks later, Jake came up with an excuse to drive to D.C. from Boston in the form of a Fantasy Football Draft with his college pals. The two had their first real date, dinner on the top of Lindsy's D.C. row house. As they shared their first kiss of the night, literal fireworks went off (it turns out the Washington Nationals had won and were celebrating at the nearby stadium but it felt like a fortuitous start to their relationship!)