Mr. Nicolay was holding his late wife Michelle when she lost her battle with melanoma as their almost 2-year old son played outside the room. A founder of Jack's Caregiver Coalition we catch up with him 5 years later in the summer of his life at 36 years old married to the new love of his life Monica. He unpacks what it's like to suddenly become a child's Dad and Mom, and how Jack's mission was born from helping him cope with the entire experience. We also explore in detail what it was like to enter the online dating world as a widower holding a kid while all the other dudes on Tinder are holding fish. He also shares simple yet profound online dating hacks that would save anyone planning to re-enter the dating world a lot of head and heart aches.