On what would have been his sister Tatiana Schlossberg's 36th birthday, Jack Schlossberg took to Instagram with a message about new beginnings. "Hey, everybody, it's May," the political commentator said in a video posted on Tuesday, May 5. "It's the month of May. I want to talk a little bit about the month of May because it's a special month. It's the month when things surprise you. When nature says, 'It's all gonna be OK.'" Small signs of life Jack Schlossberg described the small signs of life that make May different from every other month.