The match happened in May of 2020. Their first date was immediately arranged and she pulled up in her white Lexus in suspiciously oversized sunglasses and a mask, which she wore for the entire car ride. He was in a Hanes tank top and basketball shorts - befitting for the hot summer day but not exactly dressed for a first date. Their chemistry was undeniable, so much so that Simon had forgotten to ask her to be his girlfriend after months of dating and thought they were forever from then on. After a very serious lecture and confusing "What are we?" conversation - they have been inseparable since. Simon proposed to Winnie on October 21, 2024 at Taughannock falls in upstate NY (where he also thought this meant they were now husband and wife).