My Date With A Professional Dater

Being single in the city can be a great deal of fun. It’s the 21st century and I along with thousands of other semi-middle aged individuals are jumping into the digital sea of online dating. Websites like Tinder, OK Cupid, Plenty of Fish,, Lavalife, eHarmony…and the list goes on, are becoming over-populated with people looking to just have a good time or start serious relationships.

I eat, sleep, and breathe digital so it only made sense for me to give it a try.

I recently had the opportunity to sit down with a serial dater. This man was legit a professional. What he was about to tell me would blow my mind. NOTE: I originally received a message from this guy on a dating website called okcupid.


Online… don’t fail me now

For all privacy purposes, we’ll call this guy “Mike”. I met Mike at a David’s Tea at Bloor and Bathurst. I was recovering from the night before.  I had been out at a fundraiser with a group of friends and had one too many beverages. I had decided to go on the date by throwing my hair in a simple bun and wearing a cute but not overdone outfit. I put minimal effort into myself… thank goodness – I would’ve been pissed otherwise. Hungover, I trekked it onto a few streetcars to arrive at my destination.

His online photos were professionally done no doubt and I was in my own way curious to meet him. He was very charismatic and quite a cool cat. Although not my type, I’m sure several women would’ve found him a good catch. We went and sat by the U of T field and talked  about about random things for a roughly 5 minutes. Then the “What are you looking for” question came up. While I’m not even sure what I was/ am looking for, he knew exactly what he wanted.

After getting the feeling that I wasn’t all that interested in him, Mike spilled the beans. He’s been online dating for the past 3 years and is currently on 8 dating websites. Yes… you read that right..8…. He has a script prepared in which he tries to cover certain topics throughout his dates in order to get a feel for whether he wants to see the person again. Mike goes on at least 2 dates a day and up to 5 on the weekends.  He’s been on thousands of dates over the past few years. He used to tailor his initial emails but now sends out a generic email that looks like he actually took the time to read the girl’s profile. Hey – it hooked me. He’s a smart dude.




The places he takes his dates are usually the same spots. This means he is a regular at these places and the waitresses or baristas always are friendly and have his regular item ready for him. He says this gives the ladies the appeal that he’s a big deal.  He takes his dates to certain places that he has selected and knows well. One spot was a vacant condo building being built. He says this is for the more adventurous girl. Sneaking past the security gives the whole date a dangerous vibe. “What girl wouldn’t like that?’ he said. I felt like this was a slap in the face. All I got was a bench by the U of T field. It was okay though; the soccer team was practicing with shirts vs. skins. I had a nice view.


His playing field

Another spot was the TELUS building next to Varsity Field. He knows the building quite well but brings his dates on an adventure pretending to sneak around. He said this gives his dates the illusion they’re going to get caught – again inciting excitement. Was I really hearing all of this correctly? I had to pick my jaw up off of the ground a few times.

I treated the date as though I was interviewing him. I was so intrigued. What awesome material for CollegeStreet!

He messaged my girlfriend that same day as I was sitting next to her on the streetcar. I quickly told her about his deal and she was immediately intrigued but not interested in meeting him. No-brainer.

I met Mike at 11am and he was scheduled to go on another date at 1pm.  After chatting for a while, the awkward silence soon kicked in and it was time to go. We parted ways. Had I’ve spent hours getting ready, for the date, I would’ve lost it on him. He had me at a hungover state with last  night’s makeup and poorly done sock bun.Truth. Jokes on you serial dater Mike!

Mike was a nice guy who loves the ladies. He even admitted it himself that he is very promiscuous. You could call him the ultimate online ladies man. I think this is fine to a certain degree. What about the girl who is looking for love and spent 4 hours picking out her outfit and doing her hair?


Email me!

Mike is focused on his career and loves variety. He has a slight addiction to the whole thing as he rarely takes a night off. I hope that he eventually finds love. I asked him if he ever met a special girl who he would change his ways for. He said he’s met her several times but is constantly looking for something better. Being 29 and focused on your career is a great thing but money and youth will eventually run out and you’ll need someone to turn to, to give you all of the other things that money and looks cannot buy.

I think dating and not settling for something less is a smart idea however you have to give people a chance sometimes. You don’t want to miss out on something that could be great. That is what is wrong with this city when it comes to dating. Everyone is looking for the next best thing. This is myself included. I’ve dated great guys who would’ve made for awesome partners but something was missing.

The online thing can be so superfical. We base everything off of photos and short write-ups. I am a true believer in chemistry. Meeting in a bar may be sleazy and whatnot but at least there is some kind of chemistry. The smell of a man, the kiss, and the initial few minutes of meeting are all such important factors. I think within a few minutes of meeting one can instantly tell whether each party is interested.

We waste all of this time typing and texting back and forth which sometimes is all for nothing. We have a check list and everything must comply. Does he make enough? Does he have an education? Is he into baseball?

I’m not saying that online dating is a bad thing. I know several of people who have found their soul mates online. I’m just saying be careful. You might run into a ‘Mike’.


8 Responses to “My Date With A Professional Dater”

  1. wow…what an article…not all males are like this

    Posted by OakleyInc | August 26, 2013, 5:19 pm
    • Thanks for the comment! Of course I still have some faith in some of the men out there. This experience is just one of many. I’ve had several dates with awesome men who were amazing. Mike- not so much!

      Posted by collegestreetcloset | August 26, 2013, 5:24 pm
  2. This was a great read–I’m sure not so great experience! WOW. *Blank stare*.

    Posted by Sherry Martell | August 26, 2013, 5:32 pm
    • That’s the interesting thing about being in a large city. It’s full of ‘different’ Mikes…Maybe Prince Charming will come my way next week? 😉

      Posted by collegestreetcloset | August 26, 2013, 5:44 pm
  3. Okay … wow. So horrifying and yet, so freaking funny. I haven’t tried the whole online dating thing before but … wow. I actually have zero words. I think I would’ve acted the same way as you. Too hungover to really care but too intrigued to walk away. He’s like a car crash and you just want to know everything. HOW DID HE GET TURN OUT LIKE THIS? You must go on a second date … kidding, don’t (but do). Awesome read!

    -Zoe Badley

    Posted by Zoe | August 29, 2013, 4:10 pm
    • Aww Thanks Zoe! It was hard to walk away TRUST me! I have since gotten off of the whole online shenanigans… Too many of these guys out there.

      Posted by collegestreetcloset | September 3, 2013, 3:42 pm
      • Try using! I know it sounds super cheesy but one of my girlfriends uses it to meet guys because she was sick of online dating and bar hopping. I thought it was funny at first but then realized, genius! If anything it’s providing great blog content haha.

        Posted by Zoe | September 6, 2013, 3:42 pm


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