Looking for the best "Never Have I Ever" questions? We dreamed up 250 to help break the ice with new people or get to know your friends better.

Some of these titles, like Am I the Drama? and Billie Eilish’s When We All Fall Asleep, Where Do We Go?, include question marks. Others, like Olivia Newton-John’s Have You Never Been Mellow, do not.

The other day, a 60-something female, widowed client of mine received a message on Match.com from an accomplished, seemingly nice man. In her first response back to him, she asked — point blank — “Why ...