They met in Cambridge, Massachusetts at their favorite coffee shop, Tatte Bakery. Iyabo chatted him up as she prepared his drink, they ended up going out later that week and the rest is history.

On a two-week vacation, starting in Vegas and ending in Southern California, they drank and ate their way across the American West like KINGS. After finally being fully satiated from the perfect landscape, weather and cuisine, Tom took Iyabo down to the beach in Malibu and asked a stranger to take a picture of them. As he walked over to give her his phone he said "it's recording, I'm going to propose, DON'T MESS IT UP." He got on one knee and asked Iyabo to marry him, which shocked her in the best way possible. It turns out the woman Tom asked was an industry photographer and she took beautiful photos of them while they danced on the beach.