Fun Questions to Get to Know Someone

Not long ago, I was at dinner with a friend, enjoying the incredible fall weather on a patio at one of our favorite local restaurants. As we were catching up, a couple was seated at the table next to us. In order to help as many patrons enjoy the outdoor weather as possible, the tables on the patio were relatively close to one another and it was quickly apparent that they were on a first date; with body language screaming “I’m uncomfortable and uncertain of what to talk about”.

Last weekend, I was flipping through the channels and found the movie The Holiday. There was a scene where Cameron Diaz’s character (Amanda), was on a date with Jude Law’s character (Graham). Amanda was in England after a break up and staying at Graham’s sisters house for a week. Without walking through the entire movie, they ended up on a date. Amanda was asking Graham question after question until he joked that he was beginning to sweat because he felt he was on a job interview.

Perhaps you can relate to one of these scenarios and even have a similar story you could share about a moment where all you really wanted was to get to know someone, and yet you felt so awkward that you walked away not knowing much of anything about your date. The “awkward first date” and the movie scene got me thinking about some fun questions to ask that will help you get to know someone. I’ve listed some below:

• Where is your favorite place you have traveled?

The answer to this question can lead to hours of conversation and reveal a lot about a person’s travel preferences. How adventurous is the person? Do they like traveling abroad or inside the US? Hostel or hotel or tent?Tourist sightseeing or diving into the culture of the city/country?Beach or mountains?

• If you had to pick a color from the rainbow that best fits your personality, what would it be?

A silly question? YES! So what can we find in the response? Any response, other than no response, shows that a person is willing to “play.” It can also show you how creative a person is and because colors often invoke emotion, it can be a fun way to learn more about the softer/emotional side of a person.

• If you knew in college what you know now, would you keep the same major or would you choose something different?

Because we tend to spend a large amount of our waking hours at work, “what you do for a living” is often an early topic of conversation. However, just asking what someone does may not tell you much about what they are passionate about. It could be that they are extremely passionate about something completely different than how they earn their living and this question is likely to take the conversation in that direction!

• You can pick anyone in the world (dead or alive); whom would you choose to have dinner with?

So cliché! Not necessarily! The range of answers that could come to this question is endless. Their choice could give you an indication of whether history is important to them, you could learn about their feelings regarding parts of their family, perhaps political orientation, and so much more.

• Who in your family are you the most like?

In answering this question, you’ll likely learn a lot about a person’s family. However, the real bonus is learning more about your date and their personality traits from their point of view.

I’d love to hear from you. What are some of the “fun” questions that help you learn more about a person? Write me at

No Comments Yet.

Leave a reply