On Sunday, I opened Hinge and instantly matched with a brunette named Caleb.* He immediately asked me for my Instagram handle, and I happily shared it. Soon after, I got a DM: "Do you want to grab drinks sometime soon?" We agreed to get together on Tuesday, but despite my initial excitement, my interest soon withered. I later realized what had happened: Our conversation was no longer stimulating. So, I came up with 20 clever questions to DM your crush right then and there, so that you never bore the heck out of someone you're crushing on.
Don't get me wrong — learning the little things about someone new can be a vital part of developing any sort of a close relationship. But before diving into the nitty-gritty, I suggest you use social media to your advantage by asking some intriguing questions first to elicit excitement. In order to take your convo from sliding into the DMs to meeting up IRL, you'll have to establish a certain amount of chemistry. So, when you send that first message, do so with gusto — so sparks can fly.
Read on for a list of unexpected questions to DM your crush, from the carefree one-liners to the deep-dive conversation starters.