Creating a connection comes down to one important thing: questions.
And it seems in this digital age, the art of conversation has been lost and we don’t know how to ask the right questions to really get to know someone. And that’s what dating is … it’s a discovery process. And the best way to discover someone and to assess how compatible you are, is through asking the right questions.
There’s a time and place for the right questions … a time to keep it light and a time to go deep.
This doesn’t mean you can’t ask serious questions when you’re first getting to know someone. There aren’t strict rules you have to follow because things like context and tone really matter. But you probably don’t want to pull out “When was the last time you cried?” on a first date (unless it somehow comes up naturally and you really get the vibe that he’s open to talking about it …)
Tone is key. Asking him “What is one thing you’re judgmental about?” can be either lighthearted or serious depending on the context, how it’s asked, and how he chooses to respond.