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9 Questions that Will Help You Make a Real Connection on a First Date

We don’t have to tell you that first dates are reminiscent of job interviews. You return home with the basics answered – like where they went to school, what they did on the weekend, and what they do for a living – but zero sense of whether you have an actual connection

In reality, we could probably find out the answers to our common first date questions online from a Facebook profile. 

Not only do all those interview-esque questions take up precious first date time, they reveal little about the true character of the other person.

A recently published New York Times article revealed how to fall in love with anyone.

It was based on a 20-year-old study by psychologist Arthur Aron, who successfully made two strangers fall in love in his laboratory (and later marry one another). His technique was simple and involved the two subjects asking one another a series of increasingly personal questions, and then silently staring into one another’s eyes for four minutes.

Though we’re not quite sold on the science behind such love connections – and some of the questions are way too deep for a first date – it got us thinking about first date conversation in general.

Simply asking the right questions can reveal so much more about a person on a deeper level than your typical, awkward first date banter. And getting personal is the first step in discovering that potential connection you’ve been craving as of late.

 That said, here are the best questions to ask your date to get below the surface – without being a total weirdo about it.

1. “What Was the Best Part of Your Day?”
The beginning of the date will likely begin with the slightly awkward pleasantries as you settle into your seats, complete with the question of “how was your day?” After he or she replies, take it a step further and ask them what the best part of their day was. It will offer a little insight on what they place value on, and what makes them happy.

2. “Who Are Your Best Friends?”
After the inevitable question of how they spent their weekend, and subsequently how they spend their free time, make it a mission to ask who his or her best friends are. The company someone keeps reveals a lot about their character and values. Deep, long-established friendships show strong sense of devotion, while a rotating door of best friends could be a sign of instability.

3. “What Type of Child Were You?”
Once the conversation takes the natural turn of where the two of you respectively grew up, went to camp, and went to school, instead of comparing notes on potential mutual friends, ask what type of child he or she was. It could provide some understanding into the type of person he or she has become since.

4.“Who is the Most Influential Person in Your Life?”
No matter what, questions about one another’s family are normal on a first date. After you discuss the number of siblings one another has and whether respective parents are still together, ask whether he or she is close to their family, then segue nicely into asking who the most influential person is in their life. Doing so will offer clues into the type of person theywish to be themselves.

5. “What Achievement Are You Most Proud Of?”
Let’s face it; first dates are about bigging yourself up – you have a few precious hours to show you’re a great catch – whether you’re into the other person or not. After the other person gives you their resume of achievements, ask him or her what accomplishment they are most proud of, and then share yours.

6. “What Are Your Career Goals?”
When the conversation turns to work, instead of hearing them ramble on about workplace woos or challenges when it’s their turn to speak, asking what their career goals are when the office is brought up will offer a sense as to where they’ll be five years from now.

7. “What’s Your Dream Vacation?”
A normal, “safe” first date question would involve asking the other person whether they had any upcoming vacation plans. Start with that, then take it a step further and ask what their best trip so far has been and what their dream vacation would be – who knows, it may just be the same as yours.

8. “What Are You Passionate About?”
Having passions in life are an essential element to over all happiness, if you ask us. Yet, most of us leave first dates with little clue as to what the other person is passionate about, simply because we don’t ask. Asking about hobbies (how typical) reveals some passions, but passion goes beyond them – in everything from important causes to different types of music.

9. “What Are the Top Five Things You’re Looking for in a Partner?”
At this age, most of us are wise enough to gage a sense of what the other is looking for from a first date – whether that’s a relationship or a booty call. If you think that the two of you are actually looking for the same thing, get specific. Ask him/her to list the top five qualities they’re looking for in a partner – whether that’s for the night or for life.


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