Top 5 First Date Ideas

Top 5 First Date Ideas

I have been on my fair share of first dates over the past few months. Some of which I’ve shared with you in my #DatingDiary.


That being said, I have (surprisingly) been on a few awesome first dates as well!

Shocking – I know.

I’ve chatted pretty actively on Twitter about my dating life, and have engaged in conversations about first date etiquette (which we’ll get into in another post).

But for now, I thought I would share my Top 5 First Date Ideas.

These are all great, fun ideas to kind of alleviate the stress and nerves that can come with a first date.

I’m not a fan of the typical dinner and a movie date night. Not for a first date, definitely.

I mean – how can you really get to know someone when you’re sitting in a theatre – staring at a screen?

Though I’m based in Toronto, and have included local suggestions – I’m positive you can get some inspiration from this post, and look up similar ideas in your city…wherever the heck you are!

So, without further ado – here are my Top 5 First Date Ideas.

Date Idea #1 – Go Bowling

100%, one of my absolute favourite first dates. Bowling can be so much fun. It doesn’t matter how well you play, at all – you’ll have a blast. And you can forget about those first date jitters because it’s pretty hard to feel nervous when you’re laughing so much at your date and their mismatched, rented bowling shoes. Plus – cheap beer, am I right? #winning

Now – if your date shows up with their own bowling shoes and bowling ball, well – you might not have as much fun because chances are, you’re going to get your butt kicked by a pro. LOL

You can go classy and hit up The Ballroom, or – keep it simple and find the closest Bowlerama or local bowling alley near you.

Date Idea #2 – Do a Beer Tasting and/or Tour

Speaking of beer – a beer tasting can be a lot of fun. It’s laid back, casual – and, let’s face it – you’ll learn a little something!

This is a fun way to try something new and potentially avoid the huge crowds you may find at your local watering hole.

Piece of advice – don’t get drunk on your first date. It’s not cute.

You can do a tour at the Steam Whistle Brewery, do a tasting at Indie Ale House or head down to the Waterfront and hit up Amsterdam BrewHouse.

Date Idea #3 – Take a Stroll

Now that the weather is finally decent in the city – there is nothing better than taking an afternoon/early evening stroll. You can meet your date in a neighbourhood you both love, or even one you’ve never been to before. Have you always wanted to see the Degrassi High school? Meet in that area and wander around. Who knows – you may find a great hidden gem of a bar or restaurant!

There is something incredibly fun about pretending to be a tourist in your own city!

If this first date is with an utter and complete strange you are meeting off of Tinder, or something of that sort – I advise letting a friend know where you are going…just in case. Better safe than sorry! LOL

Date Idea #4 – Wine and Paint Night

Many local spots offer Wine and Paint nights. In fact, I’ve seen many on Groupon – so, you can even do it for a steal of a price! LOL Essentially, you go into a bar and it’s set up so that as you sip your wine, you paint on your canvas. This makes for an intimate setting and you and your date will be able to have a real conversation, as opposed to a loud bar where you may not hear each other very well.

And, let’s face it – if the date is a bust – at least you got yourself some new art for your walls!

Art Tonite is a great option, as well as Paint Nite. But keep your eyes peeled because small bars often offer Wine and Paint nights specifically for couples.

Date Idea #5 – Pack a Picnic

As I mentioned – now that the weather is finally better – we should enjoy as much time outside as possible. I mean, winter is just around the corner already! LOL

Grab a cooler and fill it up with nibbles and treats. You can both contribute to the options, this way you know for sure there is something you’ll like. Bring some beverages and head to a local park.

What better way to spend an afternoon than enjoying some sunshine and getting to know your date? No interruptions, no crowds fighting to get a drink order in at the bar. Just the two of you and the endless conversations you’ll hopefully have.

And if the date is terrible – at least you got to work on your tan!

Share your first date ideas with me on Twitter – @JennAndTheCity!