What’s a personal regret I’ve struggled to let go of? What’s a decision I’ve made that changed the course of my life? What’s a challenge I’ve faced that required immense courage? What’s a difficult ...

Think you know your friends and family well? Put your expertise to the test with these lightning-fast yes or no questions. Answer them rapid-fire or let the responses simmer and stew for a bit.

We’ve all been there: You’re talking to someone new, someone special — and the conversation suddenly grinds to an awkward halt. How can you keep them from saying, “Well, it’s been nice chatting with ...