Ryan and Emily initially met on a dating app but never went out. A year later, Ryan saw Emily walking downtown on the way to his office. He took the initiative to find her number and ask her on a date to dinner and a Daniel Tosh comedy show. Emily initially unsure about a lengthy date with a potential stalker received some words of encouragement from her roommate Sydney. Ryan and Emily went on the date and had the best time ever. The couple was inseparable from that day forward.