30 Tinder Dates in 30 Nights – (Part 1) Why?!

Last week I hit a low point in my dating life. I had left everything up to one guy… BIG mistake! Everyone knows you’re supposed to juggle at least three-men at a time, right? That’s what happens when you get too busy to date and rely on one man to do all the heavy lifting. You end up with nothing. And so I decided it was time to get out of my comfort zone by going on 30 dates in 30 consecutive nights. Kickoff is this Wednesday October1st, will I make it?

Out of practice…

After my very serious three-year relationship ended last spring, I found myself “back in the dating game”. But I feel like a rookie at dating, fumbling the ball all day long and making two-yard passes that end up intercepted, that’s a bad thing right? Don’t get me wrong, I had a fun summer, it was busy with social events and work, I went out on many good dates, but suddenly the whole dating thing became so tiring.

A change is gonna come…

In my effort to become more productive, I’ve been listening to The 4-Hour Work Week, by Timothy Ferriss. In his book, Tim suggest several comfort challenge exercises to get you ready to make your goals a reality. One of the comfort challenges he suggests people do is walking up to a complete stranger and ask for their phone number… Excuse me Tim? You want me to do what? First of all, I’m a very outgoing person and don’t have a problem making friends, but I’m not sure walking up to a stranger to ask for their phone number would align with everything else I’ve been taught in my life. After all, my mother always told me that boys don’t like girls who chase them.  I grew up believing that boys ask girls out, not the other way around. Not surprisingly, I spent my elementary and middle school years yearning after two boys. Neither of them had a clue I liked them because I never told them, which is probably why neither of them ever held my hand. Of course this is probably normal considering most boys at that age are interested in two things, sports and eating twinkies. Come to think of it most 30-year-old men are only interested in sports and eating twinkies.

And so I moved into my high school years, still with the idea that boys would eventually ask me out if I just walked by them enough times in the hallway or said hi every day and smiled. College was a little different mostly because I found some liquid courage. But now Tim Ferriss is asking me to approach a complete stranger, a man I might actually think is attractive and request his phone number?!

I decided to try it Tim’s way, with some modifications. My girlfriends and I went out a couple weekends ago and I enlisted their help in finding prospective targets who I could approach. This was a surprisingly difficult task because every time they pointed someone out I would think about it too long and the guy would leave or start talking to someone before I could approach. Two hours later, I finally got the courage to approach one guy, he seemed fairly normal, definitely straight and had a nice smile. So I walked up and asked a very important lead-in question: “Excuse me, are you single?”, to which he replied: “No… but cheers!”, as he raised his beer mug in my face. Ouch! That didn’t go the way Nora Ephron would have written it. “Cheers!”, I said to him as I turned and walked back to my table. An hour later we found another prospect and I approached, but he wasn’t single either. And that was the end of my comfort challenge… I never realized how hard it is to approach someone you might be interested in. But even though nothing came of it I learned a lesson, I can totally do this!

The 30-day challenge…

I wake up Sunday morning with the idea, It’s time to do something drastic. Another thing that Tim Ferriss talks about in his book is how you must set irrational or impossible goals, if you really want to achieve something great. Because most people give up too easily when the goal or the reward is simple. But the adrenaline that you get from chasing after something impossible to achieve can be enough to get you there. And so I decide to put this theory to the test. In the grand scheme of things I see this theory playing out as a successful business venture that gives me the freedom to travel the world. But given the current state of my love life, I decide to try a dating challenge first as the prefect way to get my feet wet.

At first 30 dates in 30 nights seems almost impossible. How will this even work? I do need to work, sleep and exercise as well. And what about my family and friends? I don’t want to neglect them. But the most important hurdle in my mind is how will I secure 30 dates in such short time? Without anyone’s help?

Enter Tinder…

Oh yes, I know you’re shaking your head at me and saying: “Isn’t that a hookup app?” Here’s how I see Tinder, a social experiment that you can choose to use for whatever purpose you’d like. I’ve used this app before and have met some cool people, so why not let it be my assistant in this challenge? If you haven’t heard of Tinder by now, it’s a dating or social app that lets you scroll though photos and short profiles of people in the nearby vicinity. You swipe right if you “like”, left if you don’t. If the person also likes your photo/profile then you’re a “match” and can begin chatting on the app’s platform. Where you take it from there is up to you.

On  Sunday afternoon, it takes two minutes to get my profile up and running. I invest 30 minutes of swiping and leave the app alone to do it’s matching. I return two-hours later to swipe some more… “Ooo nice eyes!” Swipe right. “Hahaha that’s my favorite Seinfeld quote!” Swipe right. “Tattoo sleeves? no thanks!” Swipe left. “Already dated a Josh.” Swipe left. “Dresses better than me.” Swipe left. “Tho is not a word and neither is cuz!” Swipe left. I quickly realize that I’m nitpicking my comfort challenge choices, which would defeat the purpose of this exercise, so I reconsider the guy who owns a chihuahua and swipe right.

I do the math and employ my sales background to figure my odds of landing these 30 dates. My past experience tells me that I have about a 1 out of three success rate so that means I’ll need between 90 – 105, for some margin of error, matches on Tinder if I want to make this work. By Sunday night I’ve accumulated my first 30. Not too shabby! I start chatting with several guys and two of them propose meeting dates. Yes!


Monday is a throwaway day thanks to my looming deadlines at work and the simple fact that I forget my cell phone at home, damn! This might create setbacks considering I’m less than 48 hours away from kickoff: October 1st. To my pleasant surprise I return home to a well-oiled Tinder machine. I have several messages on Tinder confirming dates for Wednesday, Thursday and Friday. That means Saturday night is still open, the toughest night of the week to fill with a date. Oh well, tomorrow will be a new day!



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