Drew and Rachel met through mutual friends on New Years Eve 2020. Rachel's friend Bridget and Drew's friend Ben were getting married in March and the Wedding Party got together to ring in the New Year. Rachel thought Drew was really funny and was laughing at his jokes all night long. Drew gained the courage to sit closer to Rachel and ask her about her favorite Taco Bell items and favorite kinds of sour candy. It was clear from that night they were going to get along pretty well.

Rachel wanted to wait until after their friends' wedding to go on a date with Drew. For reference, they got married on March 27th. Rachel and Drew had their first date on March 29th. She couldn't wait any longer to take him up on the date he had been asking for, for months.

Drew had been planning on asking Rachel for awhile. The plan was to ask her when they went ice skating that day. In the nervousness of the morning, he went to grab his ice skates and forgot the ring. When they got back to the house after ice skating, Drew couldn't wait any longer and grabbed the ring and asked her right there in the living room where Rachel, of course, said YES!