Dating Advice For Introverts: The Best Date Ideas To Connect Over

Dating Advice For Introverts: The Best Date Ideas To Connect Over

Dating can be fun, but for a lot of introverts, it can be a tedious task (especially in the early stages of a relationship).

These date ideas take place in less stimulating environments that will allow you to connect with your partner effortlessly.

Here are the top ten dates that I have found my introverted clients have the most fun on.

1. Library

Nice and simple. Invite your date to a library or bookstore and peruse the books together. You can take turns showing each other your favourite sections, or randomly selecting books and reading next to each other. This works surprisingly well as a first date or even as a fiftieth date.

2. Cooking Class

Step out of your comfort zone with this unique date where you get to eat your art.  Many cooking classes have cheap alternatives where you can either buy into the class through an online group buying site, or even some where you buy your own ingredients ahead of time.

What if you’re already a good cook?  Then lead your own version of a cooking class by buying the ingredients to your favourite meal ahead of time and spending a few hours with your date co-creating your masterpiece meal.


3. Runway Rendezvous

Drive out to your local airport and park under where the planes land (OFF the runway).  Lie on the hood of your car with blankets for underneath and on top of you and don’t forget to bring snacks.  Not every city has this opportunity available, but if yours does, it is well worth the drive.

4. Pool/Bowling

When was the last time you played pool?  A fun way to raise the stakes while playing pool is to attach a bet to it.  Set the parameters before you first break.  I’ve found that “best 2 out of 3” is the sweet spot that works well for dates.  It’s long enough that you get to build an emotional connection, and short enough that neither of you gets bored.

As for bowling, it’s playful, competitive, interactive, and a fun challenge to shake up the old routine.  You also get to wear nifty shoes that look like clowns designed them.

5. Seeing A Live Comedy Show

This date is great for when you feel like having a good time, but you want someone else to ‘lead’ the night conversationally. Just sit back, and enjoy the ride.

6. Art Gallery

Get caught up on culture, take in visual art, and feel fancy sipping your wine like a big kid. Again, this date is easier on you conversationally as you have conversation pieces all around you to discuss.

7. Arcade

This date is good old-fashioned fun.  Between pong, racing games, and shoot ’em up style games, you have a plethora of options as to what kind of vibe the night has.  You’d be surprised to see how far a $20 bill goes in creating memories for the two of you.

If you honed your gamer skills when you were younger and your date happens to be terrible at playing video games, ease off a little in the skill department. It’s only fun for both of you if there’s at least the chance of winning.

8. People Watching

Just like it sounds, but less criminal.  Go to the mall, a bookstore, or a public park and co-create stories about the people that you see.  Take turns (either by the person or by the sentence) creating stories about the people that you see.  It is really quite fun and flirty and you get to make fun of each other a lot in the process.  This is also a surprisingly effective way to get to know your date.  They will tell creative stories about others that will actually say more about themselves than about the people you are watching.

“See that anxious looking person over there?  They were supposed to meet a blind date here… that said they would be wearing a red sweater… but they feel like they might have been stood up.”

“See that couple walking around awkwardly?  They just had a huge fight over how he never gets to watch his Saturday morning cartoons anymore and they are trying to save face now that they’re in public.”

“See that large group of guys in matching uniforms?  They are professional golfers.”

You get the picture.  Encourage your date when she has really awesome ideas.  The more fun you have with this, the more fun you will both have.

9. Outdoor Picnic

An easy way to pass an afternoon. Pack some sandwiches, a throwing disc, and some juice boxes, and you have a quiet, intimate date for two.

10. Coffee

A modern-age classic for a reason. Get to know each other in the intellectual birthplace of some of our century’s greatest ideas.

This date is also great as a first date since “grabbing a coffee” implies less of a time investment than meeting up for a two-hour dinner.

Whatever date you choose, make sure you choose one that is congruent with your personality.  If you choose a date that stretches your comfort zone so far that you’re not enjoying yourself, it will slow down the emotional momentum in a big way.

To your success,


Want to understand what strengths you possess as an introvert? Check out this article, and see my book “The Introvert’s Guide To Dating” on Amazon Kindle, or PDF download.