While at Kayla's job on her coworker Jessica's last day of work she suggested Kayla date Drew they would be a great match and just become neighbors so they could still frequently see each other. As Jessica talked so highly of Drew Kayla's curiosity was sparked. After some Facebook stalking Kayla decided to add Drew. After a couple Facebook messages Drew finally asked her on a date. Kayla and Drew's first date consisted of dinner at Sandy Point followed by a movie of her picking (Sweet Home Alabama) her favorite. Drew and Kayla were inseparable after that first date. Drew proposed to Kayla after she returned home from a weekend away at a wedding in Connecticut for a close family friend. He surprised her by proposing in the back yard that Tuesday evening.