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It’s a brave, new, weird world of finding love online – but what happens when you use Facebook ads to try and find that love? I took a chance and found out.


“I want you to be on my dating A-Team.” It’s a muggy summer evening and I just finished typing out that message to my friend Jon. “This is the best thing I’ve heard all day. I’m definitely in – how could I not be?”

It started after lamenting the end of a relationship that I definitely got way too hung up on. Of course, like the stories always go, I was with someone amazing, but I was in the most stressful period of my life with my day job, and it really impacted the relationship.

I was having a hard time letting go because I knew she didn’t get my best. What if I hadn’t let my job get in the way? What if I had played it a little cooler?

What if she got my A-game?

That infinite list of “what-ifs” paired with a sense of what I had lost made the perfect cocktail of regrets.

“I am so terrible at dating.” I said to myself on one of those low nights. “If only I was as good at dating as I was at my job.” Lightning struck. I had a new what-if now. Could I approach dating like I approached my job? What if, instead of marketing a product, I marketed myself?

I could use Facebook to create targeted ads that would advertise me. Those ads would bring people to a landing page explaining how totally cool I am and how not-at-all sketchy this is (easier said than done, on both accounts.). The people seeing this page would be directed to send an email to a special email account I made just for this project. I’d then go on dates and find that amazing woman I was looking for.

The plan was starting to come together.


“I am so terrible at dating.” I said to myself on one of those low nights. “If only I was as good at dating as I was at my job.”


“I want you to be on my dating A-Team” – a message I would also send to my friend Desirae. “I can bring the most-established relationship angle here, so I guess I have to help you.” My friend Desirae was in. She’s been my idea of #relationshipgoals for a couple years now.

The team was coming together. Jon, who I have often called “The Tinder Whisperer” and Desirae, an amazing content marketer and writer that I really looked up to were going to help me navigate this whole insane idea. I have incredibly amazing friends (editor’s note: hashtag squad goals).

Or, I have incredibly enabling friends.

It’s a very hot afternoon; the sounds of fans in my living room are the backdrop to a Google Hangout with the team. The call boots up, and Jon, Desirae, and I are laughing about how Des is throwing out everything she owns because of some book.

I talk about a recent disappointment where I thought I was getting back together with that girl I had been seeing, and after a bit of commiserating, I ask what our next steps are. “Should I just make something and then send it your guys way to validate?” I ask.

Jon and Des are in agreement, but Des cringes in horror when I bring up the idea of creating a page on Facebook. “Oh no, you do not want to make this a social thing. That opens up a can of worms”

She brings up some serious points about how the ugly side of the internet might jump on this. Suitably scared, I decide to just make a landing page off of my current site.

Holiday Monday. I decide to kick this thing off. I start creating ads, putting in Ottawa and the age range. I then put in every random interest I can think of “Oh yeah, this girl definitely needs to like Dirty Harry, CHVRCHES, and pugs. Casablanca? Yep. Tacos, Lou Reed, Godzilla. Check, check and check. Some of my favourite craft breweries.

Emails came in and I felt an initial rush. “This is actually working.” I’m slightly amazed that someone would cross that threshold.

I reached a dilemma at this point. What did I do if there wasn’t something there, or I wasn’t attracted to the person? How do I handle this? Do I just not respond, or quietly step back after a few emails? Surely someone who would put themselves out there like that deserved better.

So, what then?

I take them on a date, and don’t go any further than that? Isn’t that a supreme waste of their time?

After a lot of thought, and some counsel from the Dating A-Team, I decided to employ something sorely underused in the realm of dating – honesty. It sucks, but if I’m not feeling it, I’ll be upfront about it and nip it in the bud.

I would later eat those words.

20 emails become 10 first dates, which becomes 5 people that you date again, which ends at one relationship. In my case, the bottom of that funnel was a teacher who we’ll call Erin.

Erin was sporty, smart, had plenty of tattoos (a big plus), and was not usually the kind of woman I went for.

Don’t get me wrong, I was attracted to Erin, and I enjoyed spending time with her; she was just far out of the realm of the kind of women I was usually with.

So real talk: one of my faults is I’m absolute shite at multitasking. I am a singular focus kind of guy, and I am relentless on that focus. This would be the first marketing sin I’d commit – never put all your eggs into one basket. You can’t rely on one channel to reach your goal.

Unfortunately that singular focus means I usually drop anything else. Call it “shiny thing syndrome”, but I prefer to call it “ruthless prioritization ”. In this instance, this manifested in me completely ghosting everyone but Erin.

Consider my words eaten.


After a lot of thought, and some counsel from the Dating A-Team, I decided to employ something sorely underused in the realm of dating – honesty.


I completely dropped the “5 people that you date again” strategy and tried to go directly to the one relationship. I tried to rush the process because I was hungry and eager.

So I focused my energy on Erin, and we spent a lot of time together. However, I had gone far too down the path before I realized that Erin had a dealbreaker for me – she never took the lead.

Now, I don’t mind taking the initiative and taking charge – but I hate to be the only one in the relationship doing so. Erin would ask me to do something, but then I’d have to follow up to make it happen, or ultimately decide what we were doing.

If I didn’t do this, we would either A) not see each other, or B) just sit around my apartment. Pardon my French, but it got exasperating as fuck.

This was to be my next sin of marketing: don’t be afraid to end it and try something different. I had put so much time and effort into Erin that I didn’t just want to call it quits, so I kept it up far longer than I should have.

By then, my ads had stopped running and I had closed the email account. The campaign had come to a close and I hadn’t reached my goal at all.

I finally got so frustrated with Erin and my overall failure that I ghosted her too. I was back to where I started. Lonely and frustrated.

This was supposed to change everything; this was supposed to be the way I was going to find that amazing person. This was supposed to be one hell of a love story.

But I forgot the cardinal rule of marketing.

There is no silver bullet.

No one thing is going to win the day – it’s a mix of little things that all work together towards one goal.

I got too wrapped up in the romance and Hollywood happy ending to see what it takes to find that special person. For most of us, it takes a lot of slogging, people who don’t text you back, and awkward hugs at the end of the night with a “it was nice to meet you”.

I’m still slogging.