They met in Fells Point as Baltimore geared up for the holiday season and end of year festivities. Emma in a Christmas bag turned chic holiday dress immediately won the attention of Riley. He was trying at the time (and failing) to corral a ragtag Marshall-Fenlon gang eager to celebrate Taylor's 21st birthday. While at Max's that night, their mutual friend Allie Fields introduced the two.

They closed the evening walking the cobblestone streets of Fells eating Baltimore's finest late-night cuisine: a pretzel dog whose buttery, flaky goodness provided Riley the necessary courage to ask for Emma's number. Bright and early the following Monday morning, Riley called on Emma to arrange their first date. Caught off-guard and without the guidance of her morning cup of coffee, Emma agreed to the date.