Wellbeing

I Tried The “52 Dates” Challenge. Here’s What I Learned.

Here’s the thing: life never goes to plan. How often do you catch yourself saying, “Oh, that went exactly as predicted”? Never.

So ‘not to plan’ is pretty much exactly how it went when I decided to do a 52 dates over 52 weeks challenge. It started on January 1. My friend Lily* and I were looking for a New Year’s Resolution. We’d both recently come out of relationships and were egging each other on. When a friend told us about the challenge, it seemed like the perfect way to get back out there and back in the dating game.

So here we were, day one, with a hell of a lot of dates to go on. Here are the rules. First, you must reach the golden 52 dates. To be clear, this is 52 dates, not 52 people. The idea was to do one date per week, but with flexibility. For example, if dates were scarce one week but in abundance the next, that was OK –as long as the 52 were reached in the end.

Secondly, you could date the same person three times and have it count towards the 52, but you weren’t able to count any more dates with the same person after that.

Thirdly, in order for a date to be a date, it had to be a meetup. This is pretty self-explanatory. If you wouldn’t call it a date: it wasn’t a date. For example a coffee or a drink, a picnic or trip to an art gallery were all fine. A pash in a club: not so fine. Well, fine, but it didn’t count towards the 52 dates.

Fourthly, you could acquire your dates in any way you liked. Tinder, a friend of a friend, a blind date set up through a colleague: all a-ok.

Everything was going swimmingly. Through the power of competition and the ongoing search for lols, we kept ourselves going strong.

Our motto was, “If it ain’t great, at least it makes for a funny story”. And there were many funny stories along the way. From Ol’ mate fireman who was in fact a real estate-agent, to Ol’ mate vet who took the liberty of offering horse tranquilisers on the first date, shortly afterwards explaining that he was in the country illegally.

There were some great dates too. Dates where the chat was easy and the lols were flowing.

And then, in true ‘nothing ever goes to plan’ style, here’s where Lily and I part ways. Only 13 dates in and I am struck down in my prime. I go on a date with one person three times. And then I stop seeing anyone else (just for a little bit, I mean I can totally catch up).

And then yep, I now have a boyfriend and am totally not going to ever be able to catch up unless I go on two dates a day, which would be absolute hell. So, I leave my single gal pal to carry the banner of singledom for the both of us. Go forth and slay, bae.

In those 13 weeks I learnt a hell of a lot about dating, though. When you have to go on all. the. dates, your survival skills improve. There were many nights where I couldn’t handle an evening of chit chat, let alone possible rejection. There were many nights where I wanted to curl up and avoid the world. But when you’ve got a number to hit, figures to achieve and data to acquire, there isn’t much choice.

So in my infinite 13-week wisdom and without further ado, I present to you the golden rulebook of dating: tips and tricks to make the process not only bearable, but safe and above all, fun.

#1 Always have an escape plan

This one is top of the list for a reason. If your date sucks, you need to make sure you don’t get stuck in it for hours. Always set up a meeting with a friend or family member 2 or 3 hours (maximum) after your date and make sure your date knows about it!

Highly recommended: make this meetup a flexible one in case you actually want to stay out with the date, duh.

#2 Get on the Find My Friends app

Don’t date alone. Someone should always know where you are, and someone should always know when you’ll be back home. I never once felt unsafe, but my housemate didn’t always know this and it helped create peace of mind.

#3 Work out what you want from it

Work out what you are dating for. And streamline your dates to match. If you’re looking for ‘the one’ and keep picking f-bois, you’re going to be disappointed.

If you want to make friends and meet new people, suggest dates that reflect this. A date at the casino followed by the strip club doesn’t scream, ‘Looking for a wholesome lifestyle. Marry me please.’

#4 Never judge a book by its cover

An oldie but a goodie. If you’re using dating apps like Tinder or Bumble, this is an important one. I’ve had many a friend wonder why Tinder isn’t working for them – and when we dive into it a bit, it comes to the surface that they’re swiping a big fat yes to all the d-bags who are more interested in their own pecs than actually meeting up for a date.

You never know what wonderful people you might meet in the world, give peeps a chance.

Hot tip: I found that most people I met up with were better looking in real life anyway.

#5 Pick people you can actually imagine having a conversation with

For this reason, bios are important, people. If you’re going to go on a date with someone, you are going to need to speak to them. Pick someone whose bio has at least one or two things you would be happy to chat about. Bonus points if you have shared interests and can get some good conversation going.

Or at the very least, if chatting isn’t your jam, pick a date where you’re actually doing something you both are interested in. Do not go ice skating if you hate ice skating. Do go to the beach if you like long walks and piña coladas.

#6 Don’t stress it 

Really, for me the purpose of 52 dates was to meet people. I wanted to go out into the world and see who was out there, what interesting stories they had to tell, what amazing things I could learn.

I was so nervous the first few dates, but quickly began to think about each date like I was meeting a new friend. I found this took the pressure of being ‘judged’ off.

#7 Use your intuition

Your intuition is a valuable tool. It is the method your brain uses to read between the lines and assess a person, it is your subconscious working overtime to tell you the miniscule details you need to know. Listen to it!

How a person makes you feel is important. If you don’t feel great in that person’s company, dash it.

#8 It’s ok to do what you want to do

Super important. This comes under the banner of being able to say no, and is essential in not dragging out shoddy dates. Never ever feel that you have to go along with something you don’t want to.

If you want to go home and take off your bra and cuddle your cat, you are entirely within your rights to say ‘this has been great, lovely to meet you, but I have to go to that thing I have to go to’ (see point #1).

In order to make dating enjoyable, you must stick to this rule, otherwise you’ll be out on innumerable rubbish dates for hours and will never want to leave the house again.

*Name has been changed.


Alexandra Longstaff is a writer, editor and stylist in Sydney. She is a yoga and nutrition enthusiast, passionate about sustainability, and she really likes her cats.