Dan and Emily met in March of 2009 at Endicott College during a party thrown by Dan and his roommates. Dan was terrified of her. Emily found it amusing and later forced him to get up on a chair and dance with her. They shared their first kiss that night. After the party, they chatted via AOL Instant Messenger (R.I.P.) for the rest of the school year. Dan came to visit Emily in Southwick after graduation and they had their first date at the very romantic Friendly's in Westfield. A few weeks later, Emily moved to Boston. They started seeing each other more and more often, becoming official that August.

In early 2016, Dan hatched a plan to propose to Emily. He got word of a tulip farm in Rhode Island where you could pick your own flowers. Knowing that tulips are Emily's favorite flower, Dan decided this would be the place he would propose. The farm was only open for 3 weeks and had a limited number of tickets available. Upon discovering that the first weekend was sold out, Dan got very upset. This completely confused Emily, who didn't realize flowers meant so much to him. They ended up getting tickets for the second weekend, but, on the way to the farm, it started to rain. Dan got upset again and yelled at the rain to stop while Emily just laughed. They spent a while at the farm, picking flowers and avoiding downpours, and when Emily was ready to go, Dan insisted on going to a final walk before leaving. For a brief second, Emily thought Dan may be about to propose but quickly pushed such a ridiculous thought out of her head. They walked to a quiet area, he pulled out the ring and asked her to marry him. She ugly cried and said "yes."