When my wife and I first began dating, we had a problem: we’d known each other already for about five years. While that was a blessing in many ways, it made that first date a little awkward. We already knew the answers to all the standard “getting-to-know-you” questions about each other (What do you do for work? How many siblings do you have? Where did you go to school? Etc.). Somehow, on our first date, we had to make the transition from friend status to couple status, and we had to jump from ice-breakers to the deeper questions right out of the gate.
While you may not share that particular hurtle on a first date, almost all of us reach a point where we run out of getting-to-know-you questions. For arguments’ sake, let’s say that occurs on about the third date. Where the conversation flowed freely and fluidly on the first one or two dates as you cycled through the standard questions with fairly easy answers, you might encounter more awkward silences by the third date as those “easy” questions have all been used up. Time to transition to some more creative—and potentially deeper—questions.
In order to assist you in moving forward with your relationship now that the preliminaries are out of the way, here are 25 questions to ask on your third date—allowing you to skip the conversational lull entirely.
- What thoughts were going through your head on our first date? Were you nervous?
- What was your first impression of me?
- Were you expecting to go on a second date? Why or why not?
- Which family member are you closest to and why?
- Do you think you’re more like your father or your mother? Why?
- What’s a period in your life that you get nostalgic over?
- What family traditions do you hope to pass on to future generations? Why?
- Are there any family heirlooms in your family that you hope to pass on?
- Describe a day in your life five years from now. What do you envision?
- What’s the best and worst date you’ve ever been on?
- Why did you choose St. ________ for your confirmation saint? (If you don’t know their confirmation saint yet, time to find out!)
- Social media: good, bad, or neutral?
- Name a saint or other historical figure you’d love to meet in person. Why’d you choose this person?
- What’s something you were afraid to do but chose to do anyway? Why? What was the result?
- If you could switch to any career/job, what would it be? Or would you keep the one you have?
- What’s the best part of your day?
- What’s a small, simple thing that makes you absurdly happy?
- Name a book or movie that’s made you cry.
- Do you believe in any cryptids (Loch Ness Monster, Bigfoot, etc.)?
- What do you think is the most important virtue to practice when you’re in a relationship?
- In what ways has your life played out the way you expected it to? In what ways has life’s journey surprised you?
- Using the format “X meets X,” what two movies best describe your life so far?
- What’s the most beautiful thing you’ve ever seen? What’s the role of beauty in life?
- What makes you feel close to God?
- What’s a hard lesson you’ve had to learn? How did you see God speaking to you through it?
The good news about third dates is that, by this time, you may feel more comfortable around your date. You aren’t complete strangers anymore, and you’re beginning to build up a store of shared memories. Conversations can deepen and connections can form. Don’t fear the awkwardness of that initial feeling that you’ve run out of things to talk about. Instead, see it as an opportunity to go deeper; there’s always more to talk about.
I have discovered this firsthand in my dating experience: even though my future wife and I knew each other pretty well and had asked all the easy questions prior to our first date, we still managed to talk for five hours! The awkwardness soon wore off, and we discovered there was so much more to learn about one another.
