They met on Jswipe. Rebekah had downloaded the app and that day Justin and her matched, and talked. She had plans to go to Bryant Park for movies in the park but as they talked he asked her if she wanted to get drinks (and karaoke) that night. She told him about her plans but could be convinced otherwise and so they met at Kiabacca in Hell's Kitchen. The latter activity never happened, as they ended up talking at the bar for 4 hours! The connection was immediate, and they both knew it wasn't going to be a typical "dating app" experience.

Justin planned to propose through a scavenger hunt. He had coordinated with her boss to let her leave work early and for her to give Rebekah the 1st clue. She called Rebekah into her office and asked her to run an errand (which was not abnormal for Rebekah, her assistant). She opened the drawer and gave Rebekah a tote bag and puzzle piece and Rebekah immediately knew what was going on. Rebekah's boss sent her on her way to her 1st stop: Bryant Park. She was told from the puzzle piece to find the fountain in the park and that's where the next piece would be waiting for her. After circling the fountain several times looking for the puzzle piece or someone she recognized, Justin's friend popped up and pointed the piece out. She was off to her next stop: Circle in the Sq Theatre. When Rebekah arrived at the theatre, she found the puzzle piece quickly but on the back it didn't specify where to go; just "the bar where we 1st met". She honestly could not remember the name of the bar and Justin's friend looked up the name and sent her on her way and... ...went to the wrong bar. She found where everyone was waiting to surprise them after Justin had proposed. When she walked in and didn't see Justin, she was confused and so was everyone who was waiting for the two of them. Rebekah's best friend from college Colleen immediately realized what was going on and dragged Rebekah out of the bar to go to the right spot -- laughing the whole way to the correct bar, "Kiabacca" 3 blocks over. Once they finally arrived, she saw Justin sitting at the table they had met at, and he proposed.