Saturday, March 12, 2011

The Dating Game: It was the best of times, it was the worst of times…


I’ll cut right to the chase here; I’ve been thinking a lot about women lately, and wondering if it’s worth it to give it another go.  My last long-term relationship ended over 5 years ago & I can count on one hand the number of times I’ve gone out with a woman (who I’m not related to or work with) since then.  Okay, more like two fingers.  I’m not complaining, but I’m not exactly jumping for joy either. 

Renee, doing the Watusi in my old apartment.  We dated in the late 90’s & didn’t have a lot in common, but at the time it didn’t matter!   

So a couple weeks ago, I saw a piece on the news that reported “1 out of 4 relationships today are from online dating sites like & eharmony.”  Really?  When I mentioned this story to a couple of friends at the office, they asked me what was I waiting for.  I reminded them that I had tried online dating several years ago (with some disastrous results), but they insisted things had changed a lot since then, it was more ‘mainstream’.  I said okay, it sounded like a plan, but I didn’t really mean it.   But ever since then, I can’t stop thinking about it.

While I’ve been on my own long enough to know I don’t have to be with someone to be content, I suppose it’d be nice to head into my retirement years, strolling down a beach at sunset with a '”seasoned” woman on my arm, you know, like in those ads put out by AARP or Viagra?  (The guy is always laughing, the woman has short silver hair & crinkly eyes, and they’re fully dressed but barefoot, with their chinos rolled up to their shins.)   Doesn’t that make a pretty picture?  If you’re my age it does!

At the same time though, I can’t help but feel I’ve had my chance & blown it.  After I finished school & moved to the city in 1990, I met & dated a nice variety of young women.   Girls like Skye (a receptionist at my company’s headquarters), Rossi (we both lived in the same apartment complex) & Renee (at a dinner party thrown by my boss).  But as nice as these girls were, I never looked at our dating as a step towards something more long lasting, like marriage.  I was too caught up in my career & making my own way in the world.  


(From left to right:  Skye, Lisa, and Renee—the girl behind the mask)

As for the online dating experience, that began around 2000 (after it hit me that I wasn’t getting any younger & I’d better try harder to meet someone more compatible).  I signed on with a very new, and for the next 6 months or so, met a whole new assortment of women:

“One Hit Wonders from”

Mary:  She worked at PNC downtown; we met for lunch, seemed to hit it off & she invited me to her house the following Friday for dinner.  When I arrived, she introduced me to her five sons (3-12 years old) that I swear I didn’t know she had.  Her oldest asked me if I knew their dad lived in the basement sometines.   No.

Donna:  She emailed me & asked me to read her profile. “Uncle Sam doesn’t want you but I do!  Career Army gal seeks man without rank or serial number”.  I was dubious, but appreciated her humor (and okay, her picture was cute).  We exchanged some letters & agreed to meet for lunch.  A couple days before our date, she called me to give me her number and asked me if I liked dogs.  When I said sure, she replied “Oh good cause I have 2 German Shepherds, King & Queenie!  Listen to this—c’mere King, say hello to Doug!”  I heard a gruff bark.  Then she said “I can wrestle King to the ground in 60 seconds, want me to prove it?”   I said “That’s not—“ and she yelled “Time!” and I heard sounds of scuffling, some grunts and finally a loud YELP!  She returned to the phone, out of breath:  “50…50 seconds!”   I congratulated her, waited a day & then made up an excuse to get out of lunch.

Shelby:  She emailed me to say she enjoyed my profile, as she had recently moved here from Jacksonville Miss & had yet to meet a “real gentleman”.  We talked on the phone & I had a funny vibe about her “Southern Lady” manner, but agreed to meet her at Market Square for lunch.   I was struck by her pretty features, but bored senseless as she droned on about “Old Daddy” and missing fresh apricots.  After the lunch, I thanked her for meeting me & she whispered in my ear “Want me to bite your pee pee?”  I said “Haha, I’ll get back to you.”  Later that night, Shelby called me in a drunken rage & yelled every obscenity in the book at me. 

There were a couple more odd ones (“Dee Dee” who was 40 online & 55 in person) and Stacey (who brought a Bible along to dinner), but then I was thankfully able to quit the service after I met someone at the office and came very close to marrying—until she dumped me for someone else!  

And now, I’m considering doing it all over again?  Stay tuned.



  1. "Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did. So throw off the bowlines, sail away from the safe harbor, catch the trade winds in your sails. Explore. Dream. Discover."
    ~ Mark Twain

    I say go for it, my friend!

  2. A lovely quote from a lovely person--thanks Becca!

  3. Wow -- these stories are not made up? Then it is true that there's just as many weird women out there as there are weird men! I thought us ladies were the only ones typically having to put with this odd behavior.

    1. Haha--wow, nice to know someone read this old post! PAM I SWEAR ON MY LIFE I DID NOT MAKE THESE WOMEN UP. Omigod--I didnt even share the "worst" ones because I didnt think anyone would believe me! Anyway, you're right--it's not just the men out there who can be weirdos! (Though, I bet women have to put up with a lot more of this sad junk then men do...) thanks for reading, Pam!

    2. Doug, seriously, you could write a book of these stories from a man's point of view. Not that I worried too much about the competition on these sites before, but if I venture into online dating again I'm definitely convinced that I have more to offer than 95% of the female population on there!


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