Single at 41

On February 5th, 2017, a Facebook ad popped up for an online dating site… wait; I shouldn’t start there.

I have never dated in my life.

Maybe that’s a better place to start.

My mom, to this day, will tell you I was always boy-crazy.  My mom, to this day, is 100% accurate.  I was recently described by my boss as having a child-like wonder around most thing that cross my path.  She described me as displaying amazement, curiosity, joy, no filter (but in a kind way) and excitement.  I have to say, my general outlook on the male species has offered equaled awe.

Whether at 8 or 38, men have always held a special spot in my soul.  But with that, my experiences never have come close to what anyone would define as “playing the field”.

I never dated in high school.  I played it safe – my imaginary love life with almost half the guys at my Catholic Secondary School was full of exciting experiences and safe outcomes.  I was pretty lucky.  I could live the fantasy and never get my heart broken.

There was this one boy when I was 17 who captured my heart like no other because for the first time, someone was ACTUALLY interested in me and we made out a lot, and he was my first love.  But after three months, he dumped me and I experienced a sadness I would not experience again until just recently.

Fast forward eight months – I starting hanging out with someone I had known for almost five years during the last month of my OAC (grade 13) year of high school.  Eight years later we married; 13 years later we separated.  One year later we are closer than we have been in years.  So, after 21 years of being in a relationship, I was officially ready to find a little companionship again.  And I needed to figure out where that was after the age of 40.

So, it was February 5, 2017, and I signed up for this “proven to work” dating app.  I put a few pictures up of me, making sure I included a full body picture because my biggest worry was someone out there accepting me as I was – plus size, but a charmer at heart! After only three days a few terrible conversations (and one picture I will never unsee), I hit it off with someone and the conversation was natural and it felt good.

He typed in full sentences.

He didn’t seem like he wanted nor needed to send me a picture of his genitalia and we seemed to always have something to chat about.

He was educated, on good terms with his ex, two kids, a great job and most importantly (in my mind), our kid-schedule aligned.

It was, what seemed, the starting of a good thing.

We texted for a couple of weeks and then a reluctant phone conversation that was a simple “goodnight” started the real person chats. A week later, this prompted me to request on a Monday afternoon to meet him at an undisclosed, ‘no trespassing’ spot mid-point to where he and I lived.

After a lifetime of never dating, I was.  And I had no fucking idea what I was doing.

Living with a lot of apprehensions, I really didn’t know what to expect, but that felt good and right and almost gitty.  I went with what was happening and I didn’t question all the shit going on in my head.

We did nothing that would follow the norm in a typical over 35 dating situation.  No drinks at a bar.  No dinners out.  No movies with popcorn and awkward holding hands.

We just did things we loved and it was new and fun and exciting and passionate and the things we experienced for months and months were great. Travel. Food. Drink. Reading. Walking. Sleeping. Laughing. Crying. Falling in love and it felt right.

And then it didn’t and it ended; a short ten months later.

For the second time in my life, I was heart broken.  I was instantly brought back to my 18 year old self; the Catholic school girl sitting on her parents’ steps not understanding what went wrong.

I couldn’t stop crying… again.  The man I had fallen in love with had fallen out of love with me and I felt lost ( I should mention, only two weeks after losing my dad).


Instead of the 18 year old me who had family around to console my aching soul and my teachers there to remind me of what I had ahead of me, I was a 41 year old, separated mom, who took a chance after never dating and was left not knowing what to do next.  A woman who, on a normal day, battled greatly with self esteem and body issues, and didn’t know how to pick herself up after being hurt so terribly.  I began to question everything that was presented to me – I didn’t know if I could ever put myself out there again in fear of getting hurt.

I was exhausted.

Here I am, just a few short weeks after and I want to be perfectly clear – I am writing this not for your pity tonight, but to remind myself, for the very first time in my life, I am prepared to stand on my own and find me; to rejoice in a love affair with the most resilient and strong person I know.  The one who has fought hard for a life she has wanted, has lost those close to her, a relationship of 21 years with two kids to boot, a career change, a new home, a new job… and most recently, a broken heart.

I am prepared to love myself in a way I have never been prepared to – wholeheartedly with no one by my side.  No distractions of dating apps or people from my past looking to connect in a way I know would be destructive.  But, just me.

I had a list of adventures I one day wanted to check off with the man I shared so many wonderful things with this last year.  I am writing these down here as a list of goals for the coming months.  And I plan on doing these on my own.

  • make homemade pasta
  • go hiking in Limehouse
  • experience another Valerie June concert
  • watch the sunset over Lake Simcoe
  • counter sex (I realize this goal would typically require a partner.  I am happy to say, to date, I can hop up on the counter on my own, unassisted.  The sex part, well, I will just need to be creative)
  • travel in an old VW van
  • give blood in honour of my dad
  • stay in a tinyhouse
  • have a weekend at the June motel
  • go ice fishing
  • enjoy a dessert at The Brain
  • wander the Deuce in NYC, imagining what it would have been like in the 70’s
  • visit Chicago
  • beat my time for a 5K

All these things will now be about me and not about me and someone else.  Because, the thing about me is, when I say I’m going to do something, I do it.

I am so ready to say good riddance to 2017. A year of so many highs, coupled with so many mindfuckery lows, that a game plan of ass kicking and having fun is really the only choice I have.

Fuck you, 2017.

2018 and I are ready to tango.

When nothing is certain, anything is possible.



2 thoughts on “Single at 41

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