How to Make Your First Dates More Fun

Two people making their first date more fun by having some wine by a lake.

Dates are only as fun as you make them. I strongly believe that. If you want to have a fun and successful first date, pay close attention to these three things—choosing the right location and activity, having a positive attitude and open-mind, and making the conversation engaging. To help you achieve this, let me tell you about a fun date I went on recently…

It was a beautiful day. There wasn’t a single cloud in the sky and the temperature was in the mid-to-high 70s. We had planned to grab coffee at a local café, but because it was so nice out, we decided to head to the lake instead.

Pick an activity that interests both of you at a location where you both feel comfortable. So yes, this entails asking your date how they feel about the activity and location beforehand versus telling them where to meet you. If you’re not sure what type of date to plan, present your date with a few options. So, if you like to hike, drink, or visit a great café (like I do), present them with these three options and you’ll immediately be able to gauge their level of interest and comfort, and then go from there. This also shows your date that you care about them, as you’re taking their interests into account and engaging them in the planning process. Furthermore, learn to be flexible when planning a first date. When you’re not flexible, your date will pick up on it and feel less comfortable around you. The best first dates are the ones where things just flow, and this starts with an open-mind and a spontaneous spirit.

As I was getting ready for the date, I listened to songs that I knew would elevate my mood, and then went over to my favorite local bakery to pick up some almond croissants to snack on at the lake. So it’s safe to say that I was in a great mood before heading to the lake. I also made sure to try and keep an open-mind and be as friendly as I could be on the date.

Go on first dates with a goal of making a new friend, not to meet your soul mate. A lot people make the mistake of approaching first dates like interviews to land a relationship. When you do this, you’re not only putting too much pressure on yourself and your date, you’re setting yourself up for disappointment, which in turn takes the fun out of dating. Do this instead—say one of childhood friends who lives in a different city tells you that one of their friends is visiting your town and wants you to meet them—treat your date like they’re a friend of a friend. This will guarantee to put you a little more at ease (and you’ll be a little less judgmental too) when getting to know your date, which allows for a better date flow.

When I got to the lake, I was pleasantly surprised to see my date had a nice big blanket to sit on and bottle of wine ready to share (it’s the small things). We exchanged pleasantries, sat down and started chatting. About 30 minutes into the date, my date asked me, “Hey, do you want to play a game?” I replied, “Hell yeah! Which one?”

Two of my favorite games to play on a date are “Never Have I Ever” and “20 Questions.” These two games are great because they not only make the conversation more thoughtful and fun, they incite honesty and build trust.

Are you up for playing “20 Questions (First Date Edition)” with me?

Ready? Here goes:

  1. If you inherited a million dollars tomorrow, what would you do with it?
  2. If you only had one album to listen to or one book to read while stranded on a remote island, which one would it be?
  3. If you could time-travel and go back to any time or period in human history, where would you go?
  4. If you could be any mythical creature, which one would you be and why?
  5. Which animal do you relate to the most and why?
  6. Who are you closest with in your family and why?
  7. How would your best friend describe you?
  8. What were you like in high school?
  9. What was your favorite cartoon as a kid?
  10. Is there any character on a TV show that you relate to the most?
  11. Which was the last movie that made you cry?
  12. Who’s your celebrity crush?
  13. What’s the most embarrassing thing that happened to you as an adult?
  14. What’s your favorite international city and why?
  15. Name one thing you’re super passionate about?
  16. What’s the last thing you learnt or skill you picked up?
  17. Who are some of your favorite philosophers or thinkers or speakers?
  18. What’s something that terrifies you and why?
  19. If money wasn’t an issue, what would your ideal first date be? You can do absolutely anything you want, what would you do?
  20. Do you have any dating pet peeves (or pet peeves in general)?

If you’re on a first date and feel like the conversation isn’t flowing as easily as you would like, try playing one of these games and/or use some of the questions above (as they cover a broad-range of fun topics) to stimulate the conversation. Just make sure you don’t ask these questions like you’re an interviewer. Listen to how your date responds to the questions, dig a little deeper by asking fun follow-up questions, and by all means go on tangents!

We ended up playing “20 Questions” on the date (in case you were wondering). And on our fourth date, we played “Never Have I Ever.”

Now, it’s your turn—Get out there and go have some fun!

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