On their second date, Bailey wanted to do something special. He made a reservation at a really nice pasta restaurant in Duluth called Va Bene. Meghan had no idea what Bailey's plans were, except that they were going out to eat. Bailey "picked" Meghan up at her dorm, and they were on their way. Bailey drove, and that's where his luck could have changed. On their way to dinner, Bailey missed a stop sign and hit an oncoming car. Everyone was safe, and the Durango only lost the bumper. Meghan had to call her family and tell them the news that the guy she was seeing was driving them to dinner and got in an accident... That was a phone call she never thought she'd have to make. The accident didn't stop Bailey from completing his mission on this date. He called a friend to come pick them up and bring them back to campus. Once on campus, they walked to The Tavern on the Hill and had their dinner date. After dinner, they went back to Meghan's dorm to watch a movie. During the movie, Bailey told Meghan he had a big question for her.... "McDonald's or Burger King?" Meghan's answer... "neither." Bailey said, "Okay, okay, actual question. Hot coffee or iced?" Meghan just laughed. Bailey finally asked if Meghan would be his girlfriend, and she, of course, said yes! Even though Bailey crashed on their second date, he didn't crash and burn in getting a girlfriend that day!

For Bailey's birthday, he chose Main Street in downtown Nisswa, MN, as the spot for a yummy dinner. But he had a sweet surprise in store. After dinner, he brought Meghan to Grand View Lodge, aiming to relive one of their favorite early dates. Their first stop was the Chocolate Ox for some ice cream, followed by a leisurely stroll around the resort's scenic grounds. Little did Meghan know, Bailey had a grand finale planned. As they made their way to the beach, Bailey poured his heart out, chatting about their future dreams and plans. Finding a cozy spot on the sand, he dropped down on one knee and popped the big question. And because he knew Meghan loved snapping pics, he'd arranged for a sneaky photographer to capture the magic moment. With the sun setting, Meghan said a big, happy "yes!"