Everyone wants to know what they “should’ and “should not” ask on a first date. The questions that are critical to ask on a first date should help you gain information and insight, but without turning a casual conversation into an interrogation.
Ready, Set, Listen!
Remember it’s not just about asking the questions, it’s about listening to the answers! That sounds obvious, but people tend to feel pressure to sell themselves on a first date. By the end, they realize they know very little about the person they just sat across from for an entire evening.
Get Past the Present
Start with questions that allow your date to talk a little bit about their past, present and future.
- Where did you grow up, where do you consider home to be?
- Tell me about your family, how often do you see them?
- What do you do on a typical weekend, any fun plans coming up?
These questions provide insight into your dates background and how they spend their free time. It’s true that you don’t just marry the person, but their whole family. It’s important to know if they like spending time with family, or is their relationship distant and strained? On the weekends, are they binging beer or Netflix, outdoors playing at the park or beach, or are they volunteering or participating in a sporting event? Does their weekend include a church or worship service? These are all things to consider when thinking about how you like to spend your time.
Get a Little Personal
Assuming the first three questions went well, it’s time to dig a little deeper. You want to know what drives them, what they value and what goals they have set for 
themselves.
- What are you passionate about – what drives you to be who you are today?
- What makes you happy or makes you laugh?
- Do you have a big audacious goal?
These questions are still conversational but a bit more probing. It’s important to know if you share humor and find joy in similar activities, if you would support their “big audacious goal” if it was to quit their job and volunteer in a third world country or hit the road in an RV for a year. Do they see themselves moving to a big city and you prefer a small-town? It should also set off warning signals if they haven’t given these questions any thought or offer up any answers. If you are a goal-oriented person with strong values and ideas, then a shaky or vague response is not going to fill you with confidence about a future.
How Do They See the World? (Literally)
These questions will help you get a sense of how they see the world and where their influences come from.
- What was your last vacation or what city/country is on your travel list?
- What was the best book you ever read (and why did it make such an impact)?
- What’s the best advice you ever received?
It’s important to know if you share a sense of adventure when it comes to new experiences and travel, or if you prefer being a homebody and staying in your safety zone. Is your date open to differing opinions, do they have positive spiritual influences who provide sound advice, do they read for leisure or more for work research? These questions can also reveal if they are workaholics and place too much emphasis on their jobs and careers.
An Attitude of Gratitude
This last question is probably one of the most important, if not the most important.
- What do you feel most grateful for in your life?
Research shows grateful people are physically, mentally and socially healthier. Grateful people have taken the time to consider the impact others have in their lives. People who are grateful say “thank you” and show appreciation to others. Gratefulness also increases spiritualism – all major religions embrace a spirit of gratitude and thanking a higher power makes people feel closer to God.
We’re often told not to get too personal, especially on a first date, but asking these questions will show that you are genuinely interested in them. If someone won’t open up or if their answers are short and guarded, that could be a sign they are too analytic or stuck in a painful emotional place or still hurting from a past relationship.
While the first date is the time to ask these important revealing questions, it’s not the time to debate their responses or judge them for their answers. It’s a chance to listen and learn to determine if you both share a vision and values. If not, that’s okay, don’t get discouraged, better to know earlier then later and you might have just made a friend in the end.
