Wow, it sucks to go through another breakup, especially as it’s been less than a year since the last one! I thought I would never date again until a 45-year-old co-worker said this to me:

“If at 45 I can go on Tinder being massively overweight, and not the best to look at, and have lots of guys wanting to date me, then so can you.”

This co-worker had been single for over a decade. She smoked heavily and swore never to date again. That was until her slightly quirky family decided to create a dating profile for her on Tinder.

She met many men on Tinder. There was:

– Tony Soprano with his gambling addiction
– There was chef with his quirkiness
– There was “Tradie” with his 30-year-old model body and six pack
– There was “bikie” who attempted a forced kiss in the middle of a dark car park

All of this got me thinking: “If a 45-year-old who claims that they are not much to look at can have success in dating, then why can’t a young buck like me sort this stuff out?”

Seeing my co-worker’s success inspired me. I vowed to set myself a goal to get this area of my life sorted out. The only problem is I become like an assassin when there’s a goal I want to achieve.

I became obsessed with this whole dating game.

I had no idea what a dating app was.

I had never sent texts to girls that I had never met in person before.

I was terrified of the potential rejection.

What did I do? I just did it anyway and you can do the same.

The myth is that dating isn’t challenging for all of us. It is. We are all afraid to date after a major breakup because we fear that we might someday die lonely.

For the next 5 months, I became obsessed with this dating goal.

I figured if I were going to reach this goal of finding someone through online dating, I would have to put in the work to shorten the time it takes. Many of my friends have been single for more than 5 years and I decided that was not going to happen to me.

I signed up for dating apps like Tinder, Bumble, Coffee Meets Bagel, eHarmony and Happn.
I went on coffee dates before work.
I went on coffee dates during lunchtime.
I went on coffee dates after work.

And then I made sure I was in the zone.

No matter the day or time I was doing something to push my dating game further.

I bought new clothes.
I bought new shoes.
I bought new aftershave.

Not to impress the girls, but to make sure I was feeling good before each date. I wanted to put in the maximum effort I could so that if I failed, I knew that I had given it everything I could.

The start was full of fear.

The first date was horrible. It was a friend of a friend that had been crowdsourced via Facebook for me. I wasn’t ready and she was not really my type. She was into pole dancing and collecting these crystals that apparently heal you or something like that. It was sooooo not me.

I rolled up to the date one hour early to ensure I didn’t miss getting car parking. I waited around until 8 pm for her. She messaged at 8 pm and said she was leaving home now and would be late. I thought to myself, “Clearly this whole dating thing is going to be hard, especially given I am obsessed with productivity and don’t like having my time wasted.”

“Instead of being pissed off, I committed not to tell myself negative stories. I became committed to not getting upset easily like most people do in life”

She finally arrived and I felt quite sick for some bizarre reason. I ordered the drinks and then she paid without me getting a chance to stop her because she felt bad for being late. This was already a mini failure as letting the girl pay on the first date is usually seen as a very bad idea.

At the end of the date, I stupidly asked for a second date and she said yes. I never ended up getting the second date and thank god for that. It did hurt my ego a little.

I then went on more than 50 dates with 50 different women.

This might seem like freaking madness but I believe that to be successful at any goal you need to get really good at your chosen task. On the first date, I sucked big time at dating. After a few dates though, I became really good at it. I figured out quickly what I wanted which I had never done before.

The fear started to dissipate and before long I was completely comfortable. I’d check the apps throughout the day to get fresh leads, meet them, narrow down the list, and then attempt to close them by asking for a second date.

My process was a lot like managing a sales pipeline through a piece of software like Salesforce. It was methodical, intentional, unwavering and organized chaos.

You can date anyone if you believe you can. You can do anything.

The reason I had failed relationships in the past was that I never thought carefully about what I wanted. I somehow thought I wasn’t good enough. Because of this belief, I limited the parameters of my dating apps only to include girls who were no more than two years younger.

I secretly wanted a younger girlfriend but never thought they would go for me. I thought I was too old and that they wouldn’t be able to relate to me. I didn’t swipe right on the good-looking profile pictures because I thought they would never go for an average looking guy like me.

Somewhere along the way when I wasn’t succeeding at my goal, I revaluated what I was doing. I realized I was selling myself short.

I started swiping on stunners.
I opened the age range right up.

To my own disbelief, I was stunned.

Amazing looking models wanted to go on dates with me. Girls that were near geniuses wanted to go on dates with me. Girls who were a lot younger than me were throwing themselves at me. It turns out that I was limiting my chances, not the real world.

The lesson here is to be careful what you filter out. You may be filtering out exactly what you want.

My friends thought I was mad.

They told me it could take 5 years. They told me I may never find someone and I needed to potentially accept this concept. I told myself this was BS. I knew that if I kept trying and didn’t let all of the fear and failure defeat me, I’d be triumphant. I visualized the day I would get my goal.

“Being obsessed with a goal looks like madness to the average Joe; the truth is that it’s how you get stuff done and get what you want in life”

Watching Netflix and saying “The universe will make it happen” doesn’t work.

There’s a lot of this “Law Of Attraction,” praise a statue mumbo jumbo that’s floating around nowadays. People say that it will happen when it’s meant to happen. This mindset will destroy your goal and any chance of being successful at dating.

“Your goal will happen when you put in the work and make it happen”

The dating gods are not going to ride in on a rainbow unicorn and give you some drop-dead gorgeous person who’s got a perfectly tanned body, and an amazing ass, with an incredible personality.

Get to work and stop allowing wet dreams to ruin your life.

Sitting on the couch numbing your brain with Netflix doesn’t work either.

Don’t let desperation overcome you.

One of the girls I met decided to go for someone else. I was shortlisted and lost. She then messaged me to tell me that after a couple of days, her new man forced her head down to the bed and wouldn’t let her leave the room.

She asked me what she should do. Naturally, I told her to leave this horrible man as violence is never acceptable. This girl came across as desperate with every interaction I had with her. She also showed me that she would make other bad decisions and then blame the world.

All of this was due to desperation. Don’t let your need of finding someone allow you to make dumb decisions. You’ll regret it later.

Never be anyone’s Plan B.

This same girl then came back to me later after she dumped this violent man and tried to go on another date with me. I’ve learned over the years that it’s never a good idea to be someone’s Plan B. If you weren’t good enough from the start, then you never will be. I told this girl no and moved on.

What I didn’t do!

Use the apps as a way to randomly sleep with as many girls as possible. In the short term this will stroke your ego; in the long term, you’ll feel like garbage. Dating is not designed to boost your ego and is far better when you concentrate on your long-term happiness.

I also didn’t attempt to date multiple girls at the same time. This doesn’t work and you’ll get found out. Lying destroys all of your hopes and dreams except you never find out that it’s the true cause. Lying gets disguised in other people’s opinions about why you failed.

You will fail if you lie or become a whore.

The problem with online dating.

You start to believe there’s always someone better. You never settle for any prospect that comes your way. The slightest thing that annoys you about the other person can make you think you should keep looking through more profiles.

One girl told me that everything about me was good but she couldn’t deal with the fact I’m vegetarian. Being this trivial is stupid.

Every person you want to date has flaws including you.
You’ll learn to love their flaws in the long-term.
Having a shopping list of wants is great way to be disappointed and remain single.

How to avoid all the pitfalls of online dating and failing at any goal.

Be relentless.
Keep trying.
Believe in yourself.
Don’t settle for second best.
Don’t look for perfect – it doesn’t exist.
Be a really nice person and treat others nicely.
Don’t try and sleep with them too quickly – you’ll trick yourself into falling for them afterward.

So here’s what happened….

I got what I wanted. I found an intelligent, beautiful, elegant little gem. She’s funny, interesting, clever, successful and has good values.

It took some time and lot’s of dates but I got there. People look at me still like I got lucky although I don’t believe in luck. I gave it everything I could and it was an emotional rollercoaster. I showed the best of me and tried to be the best human being I could.

I practiced being kind, compassionate and humble. With forced intent and continued practice, I got my goal. You can do the same.

Before I go, I want to point out that I don’t tell this very personal story I’d rather not share to make myself look good, so don’t bother leaving comments to this effect. I tell you this very personal story to inspire you to greatness and learn from my foolish mistakes.

Don’t let this negative dating world beat you down. Fight back!

If you want to increase your productivity and learn some more valuable life hacks, then join my private mailing list on timdenning.net