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Ghosts of Dating Past Part I

Pin Up Moto
Image by Lexinatrix via Flickr

35 (and over – in some cases way over)?! Why settle now? You’ve been married, divorced, had a kid or three. Why not play the field until you’re, well, 45 or so? After all, 40 is the new 30 right? What a load of bull poop.

Every birthday I give myself the first-aider once over, and thank my lucky stars that I pulled through another year. Don’t get me wrong, I don’t feel like my best days have passed me by, I know it. 

I will never again experience the drama and giggles of dumb-ass decisions like I did in my late teens and twenties. Mind you, I did take more risks than most of my peers, and I lived on the adrenaline-edge cultivated by my, “What the heck” philosophy.

Just because we dress in slightly larger and more expensive clothes than our teenagers, and keep active in such narcisistic and unique ways typical of generation X, Y, and every other generation identifier that’s come along since, are we really crazy enough not to embrace our age and the life-experience that comes with it? Maturing and Mellowing is highly under-rated.

So now, after experiencing marriage, motherhood, divorce, and living for over a decade as a “single” person again, I have a much different perspective on dating and commitment.

You see, at one point I only dated men who stood over 6’2″, had at the minimum a bachelor’s degree from a respected institution, had never been married, had never had children, and had not too much, and not too little dark hair. I had certainly acquired a taste for men who could speak more than one language, were born in another country, had professional bragging rights, and knew how to order oysters and champagne, buy jewelry and entertain me in that Great Gatsby way that so few gentlemen can pull off.  Blondes,men under 30, those with blue eyes, who didn’t reserve a date at least a week or two in advance  and a  host of others who did not meet my must have demands were left in my wake.

I went on blind dates, internet dates, managed to snag a man at each social event I attended, and many of my free weekends were taken up toasting these gentlemen with the nudge-nudge-wink-wink toast and tink of wine glasses motto that my girlfriends and I adopted, “May the Best Man Win”.

 All of this keeping in mind the sage advice I got from a much older and wiser woman on a South American beach, “Always have back-up”. In other words – keep a few on the side for those nights that would pass a heck of a lot less lonelier if you had a warm, masculine body helping to keep your sheets warm.

In retrospect, I realize that I was not dating to find a life-partner, I was dating for sport. I loved the adventure, the richness of the post-date storytelling, and the safety of not committing to one person. In retrospect a lot of the men I dated and gave a hard time to really weren’t that bad. In fact, they were actually pretty thoughtful and sweet.  I was not shy on poetry books gifted, daffodil deliveries, surprise weekends away, and inscribed jewelry. I was shy on knowing my own self, and what I had to offer.

Having convinced myself  not to settle, I have landed well, well on the other side of 35 still gloriously single.

Glorious, I say, as I reminisce about the last manI dated who turned out to be a disappointment. Realizing that maintaining “back-up” was not conducive to this thing called monogamy, I lost my list immediately.  But, as it turned out, this one couldn’t pass a mirror without flexing or checking himself out. For a man with who stood at 5’10”, he had enough confidence to convince himself that the rest of the world was responsible for his unhappiness. Yah. Alas, in my 30’s, my girlfriends and I bemoaned the age category I was now engaged in for dating/hunting.

I figure at this age, I’m either getting the sparse leftovers of the really nice guys who are now married, or waiting for the next generation of divorces and young widows. Yippee. Unless, of course, I go all-out cougar and start to give love-making lessons to the 25+ set. I need to give that some serious thought.

Previously older men were always better lovers. Now older men are almost ready to apply for Old Age Security and trim ear hair. Younger men have always been entertaining, but not satisfying. The experience was kind of like eating a tuna-fish sandwich when I really was craving lobster.Yummy. Much more satisfying than sharing naked bed space with myself, but back-up nonetheless.

I now have some hindsight about dating. It’s come at the price of a few tears, a few lonely nights, and a lot of laughs. Laughs about my own behaviour as much as any of the men that I dated.

I have entered a new phase of my life as a single person. My list of must-haves has become a few notes on what could be “general” characteristics I’m willing to explore before getting googly-eyed and romantically girly-girl over a potential partner. Don’t get me wrong, I still have expectations, I am just  much more clear about what makes a guy ok, and what makes him sphincter-centre.

Ghosts of Dating Past Part II will include a list of dating advice from someone reporting directly from the dating battlefield.

8 thoughts on “Ghosts of Dating Past Part I

  1. Without a doubt, this is a very interesting piece of writing. I am 5’9″ and I don’t know what “short man complex” is!! I am also confident and athletic. However, they way you describe your 5’10” sounds like you are very bitter over the split up and you are still not over him. This drives me to ask you why do you feel the need to belittle him and whether or not you enjoyed your intimate time with him??


  2. I was referring to 5’10″, ” I mean come on….that ‘s not short. You also very smoothly doddged my questions. Remember, there is always two sides to any story. I hope you find the one that will capture your heart. I wonder what it would take???



    1. Intimate time is just that 5’9″. That is the answer to both of your questions.Yes, there is always more than one side to any story. “The truth can be seen from many doorways” and this is my story. Capturing someone’s heart? Magic.

  3. I respect your answer. I once had a woman whom I adored despite of her insecurities, her past and her extreme jealousy. We are no l longer together because I felt I was no longer the free spirited, playful and affectionate person I had always been. I think if we carry with us the insecurities and the troubles of our past relationships we will never be able to move forward. If we truly love someone we should be able to embrace their past, present and future. We should allow ourselves to trust and approach each relationship based on who the person is and not based on what we think he may or may not be doing. if two people approach any relationship by trying to cage the free spirit of one another, the relationship will be doomed to fail.

  4. I thought am going to make one last comment on this topic. Please feel free to delete it if you don’t think it’s appropriate. After reading this piece I feel that you still have unfinished business with 5’10”. I am not sure when this relationship ended but it seems like you still don’t have closure. Therefore, you may want to have that conversation unless there was some sort of abuse or potential danger. We should have our pride in check when it comes to matters of the heart.

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