The SW Experts | These second date ideas skip the awkward
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these second date ideas skip the awkward

These second date ideas skip the awkward

these second date ideas skip the awkward

Congratz on surviving the ominous 1st date!

But what now?

It’s time for date #2 and you really want something that’s going to turn up the fun and help you not run out of conversation! Don’t worry there’s heaps of totally epic activities that help you get to know each other that aren’t awkward.

Rather than just grabbing lunch, which is basically the same as the usual dinner date, why not try one of these three outdoor adventure dates (don’t worry ‘Outdoors’ can be in the CBD!). This brings an unexpected novelty, is very chilled, and helps you see a different side of each other!

Go Geocaching

Geocaching is a real life treasure hunt that uses your phone as a map. There’s millions of these ‘treasure chests’ all over the world so there’s definitely one near you! Best of all this is still a fairly niche hobby so chances are your date’s never done it before so it will be dripping in novelty!

Here’s how it works:

Click here for video

How to make it a fun date activity:

Before the day download the Geocaching app (free) and find one that seems fun. Unless their really into the outdoors try and keep the actual hiking part of it to under an hour.

When you ask them out just tell them to wear ‘outdoor clothes’ and decent walking shoes (trust me treks in stilettos really don’t get the magic going!)

The trick is not to tell her what’s actually going to happen. This add’s an air of mystery and shows you’re an interesting person!

Pick your partner up and drive to where the Geocache suggests you start trekking. On the way explain that you’re going on a ‘treasure hunt’ that even you don’t know how to find – you’ll have to work together!

When you arrive get your phone out, load the Geocache up, and enter the ‘compass mode’. Pass your date the phone so they feel like they have ownership of what’s going on (this also means you need to talk more!)

The activity alone will generate a lot of smalltalk like:

“It says go this way”

“Oops now we’re walking further away”

“It has to be around here somewhere”

This helps reduce the second date nerves’, avoid the Superman Complex, and talk about deeper topics as well. This is particularly great if one of you is a bit shy or doesn’t talk much.

The other reason this is a legend second date is that it gives you a chance to work together as a team towards a common goal. This is an amazing window into who you both are together! E.g. Are they a really negative person? Do they love spontaneity? How fun they are sober etc…


Photo scavenger game

This is a legend way to explore your favorite nooks, laneways, and cafes with your date without just ‘meeting for coffee’.

The day before the date head to the CBD and start walking around some of your favourite spots taking a photo on your phone every 20 or so steps. Try and make each photo a little quirky and zoom in on objects to make them hard to find. Here’s some great examples of the kind of photos you want to take.

You’ll end up with about 50 photos that are like a dot-to-dot. Print these out at an office store and keep them in order.

Arrange to meet at the start of the trek and simply say it’s a ‘fun city date with a twist. This way they’ll be more mentally ready to get into it. When they arrive hand them the stack of photos and explain that it’s a scavenger game where and they’re the one connecting the dots.

Along the way stop and chat about anything interesting, grab a coffee, chat and most importantly have fun!

Add some WOW!

If you really want to wow them end the trail at:

A fancy restaurant


2pm matinee theater

An event that’s on in the city that day

You don’t need to go overboard though as it’s only a 2nd date and you don’t want to freak them out that you’re too keen – after all the scavenger hunt alone is enough to make this epic!

Chalk Chase

You’re going to be using chalk to mark a trail along the sidewalk which you’ll both ‘stumble upon’ on your way to another activity. After following the trail you’ll find some stashed ciders and a picnic lunch to chow into! This date has the added bonuses of being a really cheap date activity!

Start by finding an excuse to head to your date location like

“There’s a market on this weekend”

“There’s a cool cafe that’s just opened on the beach”

“There’s a surprise I need to show you!”

Then, about an hour before the date day begins, grab some chalk, ciders and picnic gear. Hide the ciders and food in a bush, or other out of the way spot, where others won’t find them. Then walk from where you stash them back towards the spot you’re meeting for the date. Along the way use the chalk to mark arrows pointing where to go every 20 or so steps.

It begins

When your date arrives at the beginning just act normally, as though nothing is planned, and head towards your destination.

Wait to see if they notice the arrows and if so suggest you follow where they go. You may need to point these out or pretend by asking them “have you planned something?” Either way you want to end up following the trail.

Again just keep acting normally. The chalk chase will keep the small talk coming and make way to connect at a deeper level since the awkward won’t be there!

Eventually you’re going to get to the end of the path, where they’ll realise it was you who organised it all along, and crack open the ciders and lunch. Enjoy this surprise moment and have a laugh. Afterwards head to whatever the original plan was to finish the date day out.


Do you have a favorite 2nd date of your own? I’d love to hear what makes is magic in the comments!