As copywriter for dating expert, Matthew Hussey, I wasn’t dating. (Ironic, right?) One day, I had to write an email for the dating coach, and I thought “what’s a good first date?” My mind drew a blank.

How could I write for a dating coach if my last first date was about a year ago? (Yes, I love people, but I don’t love the process of dating, nor can I can I carve out the time as I run my own business.)

So I picked up my phone, and reactivated my Inner Circle dating app. (I had deactivated it previously as it was a new app in Australia and there wasn’t a lot of members.)

Then, I began scrolling (not swiping — different interface).

I then set myself a challenge: to go on as many dates as I could in 30 days (this was December 2018), use the techniques from the dating expert that I had access to, and then write about the experience.



Why I Did This
  • To see what women experience and see how the dating coach’s programs and advice helps when put to the test in real-life situations
  • To write more effectively about their experience so I could connect better with our audience
  • To see if dating REALLY is worse that years ago

Next, I wanted to know why people were on dating apps in the first place, so I found this article on Business Insider, stating that dating apps haven’t ruined happy marriages or our ability to commit, but it may make it easier to leave an unfulfilling relationship.

So that’s good news…

My App of Choice: The Inner Circle

Marketed as “selective dating for inspiring singles who are kicking goals in their career”, The Inner Circle’s mission is to “focus more on people the like-minded people that are ambitious, and inspiring.”

Why I chose this app over others:
  • Mostly career-driven professionals who can speak in full sentences.
  • I chose this instead of a free app because I thought I’d connect better with professionals and some of the “weeding out” would be done for me.
  • Vetting process based on Facebook/LinkedIn and bots. My vetting took about 30 mins and I was targeted by a FB ad so not sure about this. This depends on how many connections you have in the app already too and if you are invited by a member of the dating app.
  • I didn’t like the “swiping by” feel of Bumble and Tinder. (Plus, I’d heard too many horror stories from those apps!)
Professions on the app
Source: The Inner Circle

And the average age of users on the app is 30 years old.

However, you need to have a full membership to see all of your matches and your messages.

OK, sign me up for a full membership at $20/week!

Now For the Good Stuff: The Suitors

You know why people don’t want to be friends with writers? Because we will write about you!

So, here’s a snapshot of the men I talked to or went on a date with…

Suitor #1

We didn’t even make it to date #1 because… well, you can read this for yourself.

  • Told me his friend said I looked mad in my profile, then proceeded to ask me if I ever had a stint in a mental asylum
  • Because I am obviously single, he asked me if the reason why I was single was because I was crazy
  • Asked me if I was a child via text when I made a joke
  • The chat felt like an interrogation rather than finding out what we are into and if we like the same things
  • Complained that women use photos that are from 10 years ago and a lot of them had put on weight. Told me he was going to start an app called “Tinder Plus 10”
  • Asked me to meet up then told me I could plan our date, and if I was already going to the city, I should come three suburbs over to HIS house.

So, in the words of Ariana Grande…

Suitor #2

I chose Suitor #2 based on his profile pic — a selfie with a baby deer which is in a wildlife park in Japan.

  • He asked me out the week we started talking. Made plans, exchanged numbers.
  • Was responsive to messages
  • Works in video production
  • Had a lot of similar job experiences
  • Came to our date one hour late but he was working AND he chose a rooftop bar that he had to walk up stairs in a moon boot as he had broken his ankle 5 weeks earlier
  • He asked me for a second date, then cancelled because work was “too crazy”. So I know that’s guy speak for “not interested”.

Suitor #3

Suitor #3 was a former lawyer, now works as an investment banker, with a child from a previous relationship.

  • Reached out to me and started talking
  • Asked me out but I was already out with Suitor #2 that week
  • Loved a lot of the same music
  • Had 10+ beers in the 6 hours we were out together, which is a red flag for me.

Suitor #4
  • Messaging and texting for a while, so I used what is termed as a“pen pals” text to gauge his interest, but he still wouldn’t ask me out, so I stopped replying as it was obvious he craved the attention


Suitor #5

Suitor #5 was younger than me, which was fine, but also, as a native English speaker, and he wasn’t, it was difficult for us to communicate.

  • Works in tax evasion strategies for a major bank
  • Plans second dates in advance — intent on impressing
  • Complimented me
  • I felt like I could be any girl he was dating, like he wasn’t selective.

Month #1 Stats
  • 5 new Instagram followers
  • 3 first dates
  • 2 second dates
  • 1 third date

Not too shabby.

What I Learned

The dating programs I had access to really worked, and helped me on the dates. I absolutely detest the process of dating. So I had to switch my mindset to think of it as “I’m going to go out to a new place for a drink and discover new places in this city,” or “I’m going to learn one thing about this person.”

Also, guys typically ask for a date (if they are interested) around five to six messages in, sometimes sooner.

But how do women do this without the strategies and ready-to-go text messages? I had all the strategies and I was exhausted.

I noticed that dating apps feed into the paradox of choice and it does mess up your head and your feeling of self-worth. On the flip side, dating apps stop the scarcity mindset ﹘ there are a LOT of great guys out there. They may not be the “forever person” you’re looking for, but they definitely restore your faith that there are wonderful, caring men out there who want the same things as you.

And I did discover that most guys (not all!) want the same thing — to find someone that they connect with and emotionally connect with.

Although I didn’t mention them as suitors here, I also went on some lovely dates with a couple of men that I genuinely enjoyed the company of and learned something from each – whether about travelling, other cultures or even tech. (But I enjoyed keeping these moments private.)

What I Did to My Profile Afterwards

I optimised my profile copy and photos (hooray for split-testing!). I change it up to see what type of guys I attract, and what kind of copy (and photos) illicit a certain response.

I did have one guy ask me if he could be my slave or servant, to which I promptly freaked out, took a screenshot, and sent it to a friend.

I also had another guy who asked me where I lived, and if lived alone (in the second message), to which I stopped replying.

So it’s safe to say: photos and copy make a difference.

“So, Have You Found Someone Yet?”

That’s the question a lot of people ask, to which I reply…


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