It's a textbook case of love at first sight. From the moment he saw her, Bradley knew that Winter was the greatest dog in the world... but to be fair, Winter's owner seemed pretty cool too. Playing Dungeons and Dragons with strangers for the first time is nerve-wracking, but Cait and Brad hit it off from Session 0. It took 4 months of adventuring before they got up the courage to do anything about whatever it was they were feeling and finally, in October 2019 they embarked on their romantic journey together. We all know what happened in 2020, but both Cait and Brad say that it's what showed them how deep their love was for one another. They both knew that this love story was worthy of a bad Hallmark movie. They rolled the dice, and it seems they both got a natural 20.