Tyler messaged first. It was about travel — Florence was planning a trip to New Zealand and Australia to visit her best friend, and he'd just gotten back from Athens, Dublin, and Rhodes. There was a lot to talk about. They talked about their language skills and music preferences. She introduced him to Stromae and Angèle. He came back with Superfly by Curtis Mayfield. Neither of them had run out of things to say by the time he left for a family trip to Europe, so he asked if she'd wait until he was back to meet. She said yes. Over the next few weeks, conversation flowed easily despite the distance (and having never met one another). He returned with chocolate from Switzerland for her.

Donna in the West Village, a server with a mysterious fixation on standing menus upright, and then Fat Cat, where they played Connect 4 until they ran out of excuses to stay. They've been together since. It's worth mentioning that he later proposed with a game of Connect 4. He had been paying attention from the start.

On October 18th, 2025, Tyler suggested a picnic at Brooklyn Bridge Park, where they'd had their third date. He'd packed a blanket, decorative pumpkins, fall leaves, a charcuterie spread, and, as it turned out, a lot more than that! At some point he pulled out a Connect 4 set — the pieces in little velvet pouches, red and yellow. He handed Florence the red pouch and asked if she wanted to go first. She let him go instead, because she's better at the game and thought it was only fair. A few moves in, Tyler took a long pause over his turn, then quietly knocked the bottom of the board and let all the pieces fall out. She told him he couldn't just start over, but reluctantly went along with it. He silently put the pieces back and continued as normal. She didn't think much of it. Florence connected four in a row in just a few more moves. He hadn't even tried to block her. He looked at her, then flipped the board around. His yellow pieces spelled out MARRY ME, surrounded by her winning red ones. Then he got down on one knee and, in broken Cantonese, asked her to marry him. She said yes, and the rest is history!