Day eighty-eight

The social experiment date

Tea with The Dater

I am almost at a loss for words.  I don’t really know how to describe my date with The Dater. I was so perplexed I completely forgot to take a photo during our date, so his photo is off of the David’s Tea website (one of our many stops in the evening, and so yummy).  It was either one of the best dates of the month, or one of the worst.  I should start from the beginning…

I met him on OkCupid, there were three messages, then I told him about the blog/book and what I am doing with the dating.  He responded with: “wow, what a douchebag move”, that he’s offended it’s not on my profile and that I’m just using him for an experiment (surprisingly the first guy to respond negatively). But, then said he’d still go on a date.  We went back and forth.  Him assuming all guys would be pissed off at me and the ones that agree are guys who can’t get dates anyhow, and me explaining that actually most guys are interested in what I’m doing, and the ones I chose to go out with are successful men who can get dates and are interesting in dating me for me.  I told him he could go on a date with me if he wanted to, but I didn’t want or need a ‘charity’ date with someone who would be angry with me the whole time.  I’m not sure what made me keep responding, but there was something about him I found challenging and interesting.  Then he said he was busy until the end of the month and I figured I’d never hear from him again.

Well, I did and we set up the date for last night.  He offered to pick me up from my house.  I was already weary of the date, so there was no way I was going to give him my address.  I even told a friend where we were going, just in case he ended up going crazy on me and I needed someone to rescue me.  I don’t really know what it was about him, though, but I still wanted to find out what he was about.

We ended up spending just under four hours together, talking the whole time – Indian food at King Palace (amazing food on Church, east of Yonge), walking to the Cameron House (we got there between sets of live music, so just had a drink), walked to David’s Tea, people watched, then ended the night with a final drink at the Elephant & Castle pub.  The Dater (he is an active dater, even admitting to needing cheat sheets when he dated a lot years ago to keep the girls straight – he has recently broken up with a long-term partner, so is back to dating) told me tons about his life and I also shared more than I normally do on a first date.  He has a sarcastic, dry sense of humour that makes for really interesting conversations paired with my gullible nature.  He made me laugh a lot (especially when he said I was very innocent – little does he know…).  I think we grew on each other, considering we were both a little weary of the situation at first.

The weird thing is, I felt a bit like I was in a social experiment of his own.  He is definitely an expert in dating and had ways to ask questions to get the responses he wanted to assess me.  And his paranoia about my experiment started to make me paranoid – was this a game for him?

At the same time, he challenges and intrigues me.  I had a lot of fun.  And he’s pretty cute.  He was definitely one of the most interesting dates I’ve had.  I want to hang out with him again to figure him out a bit more.  And I feel like he could teach me a thing or two about the art of dating (a skill I’m not sure I’ve learned, even after twenty-six days of dating – but then, maybe being genuine and the ability to connect with people are the only skills I need).


Priorities… (will explain more tomorrow)

Day eighty-four

Another OKCupid date

Me through the app designed by Shiny Shoes

He’s been sky diving a couple of times, white water rafting, hiking with black bears, and exploring Alaska.  He can’t wait to visit New Zealand to bungee jump.  He was born in India, lived in New York for years, but loves Toronto.  And he didn’t read the blog before coming on the date with me!  Shiny Shoes is an adventurous man.

I love inside jokes.  They instantly make a first date comfortable.  It’s an easy thing to bring up to remember the banter (online, over the phone or by text) that made you excited about the date in the first place.  We had a running gag involving him shining his shoes to get ready for the date, and sure enough he showed up with shiny shoes!  I loved it!

Brunch together was fun, although it turns out I didn’t explain my year as much as I thought I had online, so I spent a lot of time explaining what I’m doing.

He was really great and I loved hearing about his adventures.  So, I’m not sure whether it was the tired thing (from my day of dates the day before), or chemistry, but I didn’t feel a romantic match.  That happens – a lot, I’ve found out.  Even if you like the person on paper, the conversation is good, they are an attractive person with good manners, and you have things in common, doesn’t make for a romantic spark.  It’s as much about timing and a feeling you get that makes them someone you want to date further.

More in online dating…

There are a few things happening in the online dating world that I haven’t talked about yet and thought I’d touch on, as I’m not sure they will turn into dates.  I’ve met a couple of great people who I thought I had a connection with, but once I mentioned the blog, they backed right off.  Even one who dates bloggers on a regular basis (although he said to call him for home-made perogies next month, if I didn’t find a love match).  I’ve had a few who seem keen to go on a date with me, but then keep putting it off because they are busy or away.  I’m not sure whether they are getting cold feet, lost interest or are actually busy, but I do hear this happens a lot in the dating world (although now I’m close to being booked up for the rest of the month).

I’ve also met one really interesting man who is in a 10-year open relationship with his wife and mother of his children.  I’ve told him that I couldn’t be “the other woman”, even if his wife is into it, but I am fascinated by the concept and he agreed to answer a bunch of my questions about the lifestyle.  If I can get his permission, I will post some of his answers by the end of the month.  He did steer me towards a couple of swingers websites, though, so if anyone is interested (I’m warning you, these are rated-r websites): Fling in the City (hosted by Wicked, Toronto’s first hedonistic on-premise club) and Ontario Couples.  This is a huge section of dating that I probably won’t get the chance to explore this month, but I thought should be mentioned.


Lunch with a friend of a friend I met at a party last month who volunteered to be one of my dates without hearing much about the project.  I’m looking forward to this one, as this is our third attempt to get together.

Day seventy-nine

The online-Facebook-blog-YouTube-text-finally-meeting-in-person date

The Eco-comedian. Yes, he picks up used batteries to recycle them.

The Eco-comedian first contacted me on OkCupid with a shameless plug for his YouTube page.  I watched some of his stuff and thought it was funny, so I became his fan on Facebook.  Then I plugged my blog.  He invited me to the Green Party party on election night, so we exchanged phone numbers to meet up (which we never did).  We became Facebook friends and either messaged or texted back and forth for the last few weeks.  He asks me how the dates are going.  I ask him how his mission to unite the political left in Canada by writing a song to Jack Layton is going (he’s written love songs to Green Party leader Elizabeth May and environmentalist Laurie David – see below).

Finally, after seventeen days, we met for pizza during his lunch hour from his job at an ad agency.  He wore dark sunglasses and a hat, so I didn’t recognize him at first, but I also felt like I already knew him.  He’s a pretty funny guy.  And really into eco issues.  He’s made a name for himself writing songs and doing videos that are fun and make people aware of environmental concerns.  He also does podcasts, interviews, and radio.  He’s a busy man.  And he’s going to help me make a couple of videos for 3hundred66days, which is awesome.

In honour of his constant shameless plugging of his work, and because I think this video is hilarious, The Eco-comedian will be my first non-anonymous date of the month.  Here is his video proposal to Laurie David, when she was divorcing from Larry David (of Curb Your Enthusiasm fame):


Speed Dating!  I’m really nervous.  I was checking out the questions they suggest and they remind me of interview questions.  I hate interviews!

Try to find out about the person the things that you would need to know in order to want to pursue your connection further, or not. Here are a few fun questions below:

  1. What makes you happy, brings joy to your life?
  2. What do you do on a typical Saturday or Sunday?
  3. Do you believe in love at first sight?
  4. What is the most dangerous thing you have ever done?
  5. What was the funniest thing that has ever happened to you?
  6. Have you ever had a life-changing experience?
  7. What do you think is the most misunderstood thing about your gender by the opposite sex?
  8. What positive quality do you possess that you also look for in others?
  9. Where do you see yourself in five years?
  10. If you could only eat one food for 3 days in a row, what would it be?

Check out all their “fun” questions at

Day seventy-eight

The (former)teacher-(former)student date

The Teacher

When I dropped out of The Teacher’s improvisation class last year, I wasn’t his biggest fan.  The intro improv class with a different teacher was fun.  Moving to the next step up, with The Teacher as my instructor, was painful, vulnerable and too much of a jump for me.  I dreaded going in to the class to put myself in that position.  And I blamed The Teacher.

When he added me as a “favourite” on OkCupid, I recognized his photo from his Facebook profile (he’s friends with 2,502 people).  I immediately wrote to him: “I know you. I took a class with you at [name of improv company]. And we’re Facebook friends (although I know you have 3 billion facebook friends because every time someone adds me as a friend, you end up as our mutual friend!)”.  I also mentioned a real-life mutual friend we have and that another friend of mine (and former student) used to have a crush on him.  After him finding me on Facebook, I received this answer: ” I found it. Also, found out about this whole blog thing. Very intriguing. I’m a great date, if you need someone to fill a day AND I don’t like cucumbers” (making reference to the guy who told me to f__k a cucumber).  And so the idea for a date between former teacher and former student (of three classes) was born.

I wasn’t sure what to expect on our date.  It actually turned out awesome.  We have tons in common and chatted about theatre, life, hand gliding, using improv skills in the workplace, growing up, writing.  A quick lunch turned into two and a bit hours of chatting – an hour after he had paid the bill (which was very nice of him) and we had nothing in front of us.  He was quite charming.  The only awkward moments were the same that are on every date (see below).  So a surprisingly enjoyable time.

The awkward moments of a date

From the sixteen days of dating that I have experienced this month, I have learned that there are always three awkward moments on a date:

  1. The first five minutes:  Do you hug?  Shake hands?  Smile and nod?  Kiss on the cheek (one of my favourite dates this month started with a kiss on the cheek)? Is it going to go well?  What will you talk about first?  What does your body language say?  What does his?
  2. “Can I take a photo of one of your body parts for my blog?” (I need to work of the phrasing of that!): Always an awkward moment reminding both of us I’m writing the blog and me having to get out my camera and decide on what to take a photo of.
  3. The last five minutes: Do you hug?  Shake hands?  Smile and nod?  Kiss?  On the cheek?  On the mouth?  Do you mention that you’ll talk again?    Do you talk about a possible second date?  Do you not talk about this?
I hope by the end of this month I have some advice to give everyone about how to deal with these awkward moments (well, maybe not the 2nd one as I’m pretty sure everyone doesn’t take archival photos of their date’s body part…).


Lunch with an eco-comedian who I met online and have texted and messaged back and forth so many times I feel like I already know him!

Day sixty-nine

The online date

The Intellectual (well, his shoe and my shoe together)

My first online date of the month and such a positive experience.  I’m going to have to try to set-up bad dates for the drama of it! The Intellectual was absolutely lovely.  Kissed me on the cheek when we met, had a whole day planned of seeing exhibits from the Contact Photography Festival (including a route plan – what TTC to take and addresses of galleries), and even bought me ice cream from an ice cream truck on the side of the road (where the older Italian man selling the ice cream told him he couldn’t have the ice cream cookie that he wanted because it was messy, winked at me, and instead gave him vanilla.  I, on the other hand, could have whatever I wanted!).  We had some great discussions about sustainability (he runs a blog to increase discussion about sustainability), human suffering, social behaviours, unions in America in the 1970’s (brought on by a film he just watched), and silly things we used to do as children.  He reminded me so much of an old friend of mine that I instantly felt at ease.

Meeting someone for the first time is always a little hard.  What do you talk about?  Can you reveal too much about yourself?  Or too little?  We seemed to fill the time quite well.  He has some fascinating viewpoints on the world and I enjoyed asking him questions to get in-depth responses.  It was definitely a getting-to-know each other day, and hard to tell whether there was a romantic spark or a friendship one, but I enjoyed the day and didn’t want to leave to go to work.

More about online dating, for your info…

There are many online dating sites that one can use in Toronto.  Some of them you need to pay to use: eHarmony, Lavalife,  Some are free (which are the ones I have used): PlentyOfFish, OkCupid.  I signed up for PlentyOfFish a few months ago to try it out and do some pre-research.  The reputation of PlentyOfFish is that it is used for sexual hook-ups.  Although I did find some decent guys on there (one who I went on two dates with and decided he would be great for my best friend), my first experience with online dating was crazy.  I kept a journal while I was starting out and here is an excerpt of how I was feeling during the time:

It’s the morning after I signed up for online dating and I already have 5 messages and 5 other people who “want to meet me” (one of which is named “let me eat that asssss”!).  In all honesty, I’m not sure I’m ready for this.  Maybe online dating should be a last resort, not a first.  But I have to give it a fair shot.  What is it with the messages that only say “hi, how are you?” or “hi how r u”?  Why do I want to respond to those?  Is that what people do on this thing?  And my favourite message so far: “eeeeeeeeeeeeeeeh hey to cold for u i am stack here what would u DO ON the first date>>>>>>>>>>” What does that even mean?!

I signed up to OkCupid at the beginning of this month and I’ve had way more success with that.  The guys seem more genuine and I’ve been messaging with some really interesting people so far.  I love really unique intros too.  One guy sent me a recipe.  Another corrected a spelling mistake in my profile (every writer needs a good editor).  A few have asked about certain bands I wrote in my profile, or photography, or theatre.  At first I tried to respond to everyone who sent me a message, but now that’s getting hard.  It’s so time consuming, I don’t know how people do the online dating thing and still are able to work and have a life.


My first ever boyfriend and first kiss.