Amy had been good friends with Ms. McDonald since they had stayed working together at BBMS. One day back in 2008, Ms McDonald asked Amy and her roommate at the time, Nina, to come over for a BBQ. Ms. McDonald wanted to introduce Amy to one of Jeff's friends, who she believed might be a good match for her. Well, that was a flop, but Amy and Jeff kind of hit it off! Unfortunately, Jeff was involved with someone else at that time. A few years went by with little communication between the two until Amy heard that Jeff was single again. She took the opportunity to wish him good luck as he entered the fire service, liked a few Facebook posts, and planned to make it to the annual Marti Gras party. Jeff was planning very similarly and that night the two spent the whole evening together laughing and enjoying themselves.

Jeff and Amy met up at a few group events, but the real first date wasn't until the end of February 2013. Amy was excited because Jeff called one evening to suggest ice skating, followed by drinks and dinner. This date was right up Amy's ally. They first went to Rockville Towne Square where they rented skates and Jeff showed off his skills (and did his best not to laugh at Amy's coordination issues). Then Amy convinced Jeff to cancel their reservations at American Tap Room and they went to Gordon Beirch instead. After a dinner full of laughs and stories, they decided to go see a band at Growlers, where they realized their mutual love for dancing (and drinking), and ultimately each other.

Amy's parents Pam and Bruce surprised Jeff and Amy with a vacation to Aruba for Christmas. Both were very excited to get out of town and spend some time in paradise. By February, Jeff realized that this would be a great opportunity to pop the question. Jeff took a few design ideas that Amy had hinted about for months over to Aras in Rockville and had a beautiful custom ring made. The day before the big trip, Amy and Jeff were running errands when the jeweler called Jeff to ask when/where to send the appraisal, which Jeff played off as a call from his stations rookie asking annoying questions. He was very angry with them for contacting him and was sure that Amy was starting to realize something was up (she wasn't). The day of the trip arrived and they headed to the airport. While Amy was battling with the check in Kiosk, Jeff made sure the ring was still in his carryon in a handkerchief. It was, until he messed with it and the ring came flying out of the bag, bouncing on the floor. Now Jeff was sure Amy knew something (she still didn't). He quickly recovered the ring and they went through security. They arrived in Aruba and caught the bus for the Radisson. When they arrived, the room wasn't ready, and the desk staff tried to make a last minute switch to a king size room. Jeff had arranged for some champagne and strawberries to be in the room, but with the last minute fumble, that wasn't going to happen. Jeff and Amy decided to just change into swimsuits in the bathroom and hit the beach for a drink until the room was ready. Carry-ons still in hand they stopped at the bar for a Balashi and a fruity cocktail. They walked down to put their feet in the water and as soon as Amy stared out at the beautiful ocean and took a deep breath, Jeff said, "Amy, will you marry me?" and pulled a handkerchief out of his pocket. Amy started breathing hard and didn't understand what was happening and didn't answer for several seconds. Jeff hesitated, then said, "Oh, I guess I should get on one knee," so he squatted a knee in the water. Amy finally came to and said "yes, of course yes!" The beach was packed with people, but no one noticed that the two weirdos with their carry-ons on the beach lives had just changed forever!