Bennett and Isaac first met while Bennett was visiting his sister at Brandeis and made Wacky Mac in Isaac's Mod, and while they both thought the other was cute, neither one made any move. Famously, this wedding's officiant, Yael Jaffe, told them that they wouldn't be good together. However, in the midst of the pandemic, while on a rooftop meal, Isaac asked famous friend Alissa Fagin if "Simmy's brother" was single, and she reached out to Simmy Decker, who talked to Bennett. They texted for a while, but when Isaac tried to make a Zoom date happen (Bennett was living in Philadelphia at the time), Bennett had to postpone because he was going to organize counterprotests after the 2020 election. Isaac, remarkably, was okay with this extra-ness (as he continues to be to this day), and the two went on their first Zoom date a little over a week after the election. After 9 months of Zoom dating (do not recommend!) Bennett finally moved to New York, one thing led to another, Bennett proposed at a Mets-Phillies game, and they are so excited to get married this January!