Sara and Kyle first met in New York City in 2019. They swiped on each other on multiple dating apps starting in January 2019. However, the two were finally able to have their first date in July 2019 going to Rare rooftop in New York City. After drinks overlooking the city, the couple decided to finish the night at the local jazz bar the Flatiron Room. Sara was impressed by Kyle's charm and creative date ideas, while Kyle was smitten over Sara's "natural smile". The two decided to make themselves an official couple on October 17th, 2019 while they were out at a show in downtown Manhattan. Throughout their relationship the two bonded over being foodies, traveling, and trying new and exciting activities.

On October 17th 2021, Sara and Kyle were celebrating their 2 year anniversary. Kyle surprised Sara with a boat ride along the Hudson River. While in between the Brooklyn and Manhattan Bridge the "first mate" on the boat advised the couple to take a photo at the edge of the boat as the bridges make for a great photo. While the two were standing at the edge of the boat, Kyle got down on one knee and asked Sara to marry him. Sara said yes of course! The two then set sail along the river to the Statue of Liberty celebrating with their favorite wine. After the two finished their boat ride, Kyle surprised Sara with dinner and drinks at the Flatiron Room (their favorite jazz bar they went to on their first date). When they arrived Sara was surprised by several of her friends, where they celebrated the news.