Jenna and Drew went on dozens of bad Hinge dates before finally matching with each other. After weeks of talking and getting to know each other they finally picked a date to meet. Drew and Jenna had their first date at Elsa Cocktail bar on a hot Brooklyn evening. When Jenna walked into the bar she saw Drew sitting at a booth, drink in hand with the biggest smile on his face. Jenna and Drew connected over their love for their family, friends and roast chicken. Jenna and Drew felt an amazing connection on their first date and had a gut feeling they had to continue to see each other.They have been happily together ever since.

Jenna and Drew planned a week long vacation to celebrate the end of the school year in Mexico. Drew was adamant about going on this trip but realized his passport expired. Jenna noticed how stressed Drew was about this but it never crossed her mind that he had far more than his passport on his mind. Luckily the passport drama was resolved and Drew and Jenna got to the resort without an issue. Champagne was waiting and Jenna was greeted by the resort staff with the name Mrs. Roberts. Although Jenna liked the sound of that she figured that was years away and had no idea what was coming. When they got to their room, Drew made Jenna wait on the balcony as soon as they walked in. Although Jenna thought it was weird, she listened to Drew's suggestion. Moments later Drew came out to the balcony while Jenna was putting on sunscreen and started saying suspiciously sweet things. Before she knew it Drew opened up a shiny box and asked Jenna to marry him. It was truly the best surprise ever.