Vanessa met Samantha, Jaime’s sister, at Stacked Bar, where she decided Vanessa should date her brother. Mind you, Vanessa was dressed as Strawberry Shortcake for Halloween. She showed Vanessa his Instagram, and Vanessa immediately realized he had a picture with her brother-in-law, Isaac - who Vanessa was living with at the time. Jaime was in Chicago for work that night, but Samantha told him to follow Vanessa on Instagram anyway. He did. Vanessa asked her sister, Seb about him, and she confirmed he was “a nice guy”. Vanessa & Jaime followed each other for a full week with zero interaction—clearly two confident adults. The next weekend, Jaime and Isaac were both groomsmen in Jaime’s cousins wedding. At the reception, Jaime learned a lot about Vanessa from Seb which convinced Jaime to ask Vanessa out. That Monday, he sent Vanessa a voice memo on Instagram, saying “I heard a lot of great things about you” & it ultimately led to him asking Vanessa out on a date… that same day. Apparently, all it takes to meet your future spouse is two determined sisters, a cousins wedding, a brother-in-law with a childhood best friend, and a well-timed voice memo.