Hailey was traveling home from the Cayman Islands where she was vacationing with her mom and grandfather. Matt was commuting home from work as he was based in Fort Lauderdale as an airline Pilot. Matt walked on the plane and sat right across the isle from Hailey. They glanced over making eye contact a few times but no one said anything. When they landed in Tampa, Hailey was the first one off the plane as she had to use the bathroom (shocker). Matt thought his opportunity to speak to her was gone, until she walked on the tram that took them over to baggage claim. Matt struck up a conversation with Hailey and as it turned out, they lived a block away from each other. They went out that night and have been together ever since.

Matt and Hailey, again on Southwest flight, were traveling home from Nashville where they were vacationing with friends for Hailey's birthday. Throughout the weekend, Matt had various bands pull Hailey on stage to sing Happy Birthday to her. Leave it to Matt to convince the Flight Attendants to do the same on their flight home. Hailey had gotten up to visit the restroom and when she got back to her seat, she noticed Matt up front in the galley with the Flight Attendants. They called Hailey up to the front and proceeded to enlist the whole airplane to sing her Happy Birthday, again. Matt made a little speech over the PA system and had Hailey turn around to say thank you to the passengers. It was when she turned back around to face him, that he was down on one knee asking her to marry him. She said: "Wait really?" Followed by a "YES!"