LeeAnn & Chris matched on an online dating site and, after a plethora of failed first encounters with other would be suitors, decided to throw caution to the wind and have their first date on Valentine's Day 2018. They didn't entirely throw caution to the wind, however. They mutually decided that going to a nice restaurant on the high Hallmark holiday might put a bit too much pressure on a first meeting. Not to mention potentially be a waste of money -- I mean, what are the odds they're going to see each other again?! Instead, they went to Biddy Early's, a dive bar in the Financial District. After a couple of drinks, some sandwiches and fries, and a few hours of great conversation, they decided to see each other again and, well, here we are!

LeeAnn gave Chris a difficult task when it came to popping the big question, telling him she wanted to be "totally prepared, and yet completely surprised." Chris managed to pull it off. After the pair picked out a ring together in May, it lived in Chris' drawer for a couple of months until August 12. Chris didn't know that day that it would be the day he asked LeeAnn to marry him. They enjoyed a night out with friends at Grill 23 (their taste in restaurants improved after the first date) and, when they got home, Chris knelt down and asked her to be his wife when they were together in their apartment. LeeAnn asked, "is this real?" several times, but somewhere in the midst of her surprise, she said "yes."