The '36 Questions for Closeness' T-shirt is based on a study called "The Experimental Generation of Interpersonal Closeness" by Arthur Aron, Edward Melinat, Elaine N. Aron, Robert Darrin Vallone, Renee J. Bator published in 1997, which concerned itself with accelerating the feeling of closeness between two people when using these 36 questions. The study gained more attention when the 'New York Times' writer Daniel Jones posted an article about it in 2015 titled 'The 36 Questions That Lead To Love', discussing the potential of asking these questions on a date and falling in love with each other.
Supposedly, two people that took part in the original study ended up falling in love and marrying each other - but don't worry, this is just as fun with a friend or a casual date.