50 First Dates

I realized several months ago that I had never actually dated for fun in my life.

I was like Scarlett O’Hara in the first four seconds of this scene from Gone With the Wind (sub the word “dating” for “marriage”):

“Dating, fun?  Fiddle-dee-dee.  Fun for men, you mean.”

I was raised that you marry the people you date, and from an early age that seemed to be what dating was all about.  Talk about pressure.  There was pressure to find an eternal mate, and pressure to not hang out.  Date.  Date.  Date.  It felt like a chore.  Worse, I felt like I was holding down the worst Human Resources job in the world.  Here I was trying to find  and interview for a new CEO, but holding applications for guys that were just looking to get their foot in the door to earn some extra cash.  Not that there weren’t some great CEOs-in-the-making among the applicants…

So during times in my life when I wasn’t particularly interested in settling down, I didn’t date at all.  It seemed disingenuous.  Wasn’t everyone looking for marriage?  Isn’t that why they were dating?  As a result, nearly every date I’ve ever been on has resulted in a relationship (and not necessarily a good one).  There has been the odd exception here or there, but those cases were rare.  The exceptions that proved the rule:  I didn’t know how to date for fun.  Once.

Until now.

This year I decided would be different.  I changed my mindset and decided to make it all about having fun.  50 times over.  No pressure for a second date (not that I wouldn’t welcome one; that just isn’t the goal).  The goal is for both of us to have fun.

So I posted the following Facebook status update:

it recently occurred to me that i have NEVER dated just for the fun of going on a date… and now i really want to x50. my goal is to go on 50 first dates this year. i am perfectly willing to travel.

i am sorry, but if we have ever been on a date before, or if you are married or otherwise in a committed relationship, you are not eligible for this limited time promotional offer. everyone else is fair game… so if you’ve been harboring a secret crush on me for years, now is your chance!

In less than ten minutes, I had two genuine offers for dates.  And so it began…

… Until I hit my head and wound up with a concussion.  Just as I was getting excited, too.  I had to put off my quest to find 50 first dates until I healed.

1 – Nobody wants to go on a “light-duty” date.  Sorry, no movies, loud noises, bright lights, roller coasters, zip lining, or anything that involves physical activity beyond walking.  Ugh.  That would pretty much leave the job interview/interrogation date.  No, thank you.

B – I couldn’t line up dates if I’d wanted to… I couldn’t look at a screen for more than five minutes during the first two weeks without getting a massive headache.

As it turns out, I had more than 30 emails awaiting responses on my two online dating profile accounts.  Whoa.  That took up an entire weekend.

But, I’m ready now.  Let’s do this!

Behold.  The Little Black Phone.
Behold. The Little Black Phone.


Are you going to blog about your dates?

Of course, I will be blogging about the dates.  However, to protect the identities of my dates, I will change whatever information I choose.  They know who they are, but that doesn’t mean they want the rest of you to know.

Are you accepting blind dates/set-ups?

Definitely.  I have to make it to 50 somehow.  But please don’t set unrealistic expectations for either of us… “OMGoodness!  You have to meet so-and-so.  They are perfect for you!”  Clearly, if that’s true, we’ll figure it out pretty quickly.

Who is paying for your travel?

I expect that I am.  Not that I wouldn’t be perfectly willing for someone else to foot the bill, but I intend to cover my own travel expenses.  They have enough to worry about with planning an awesome date, right?  Travel dates will probably be a lot less frequent due to the added costs and complications.  I already have three pending; one is set, and two are trying to coordinate schedules.

Even international travel?

If someone is brave enough to ask, and I can swing it with my schedule and finances, I don’t see why not.  One of the greatest first date experiences I’ve ever had was Istanbul, Turkey.  That one probably won’t be topped.  It’s probably best not to try.  I can have just as much fun building a model rocket as long as there is good company to be had.  Oh yeah, and my passport expires this year, so I’ll definitely be out of the international travel game until the new one shows up.

Istanbul, Not Constantinople
Istanbul, Not Constantinople

What about Josh Groban; I thought you guys had something special?

We totally do.  Bonus points to anyone that convinces him to take me on a first date this year.

Can I share this post?

Do chickens wish they could fly?  Only always.

I'm Waiting.
I’m Waiting.
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10 Responses to 50 First Dates

  1. Walter says:

    Darn my reluctance for logging into Facebook. Not really reluctance but more like apathy. I’m sure my three friends don’t mind the lack of updates. Besides, Facebook is clingy. You don’t log in for a bit and you receive those “people you may know” emails. If that doesn’t work, Facebook will try to pique your interest with the “you have one photo tag” messages even when you don’t have any new tags. I don’t respect that. Can’t we just be acquaintances that acknowledge each other when our paths cross Facebook?

    Where was I? Oh yes, darn my missing my opportunity on Facebook. Wait. I’m married. It is just as well. My idea of a good date is racing those motorized carts at Walmart at 3am.

    Just kidding. The last time I was up at 3am was when my wife was sick, two or three days ago. Don’t worry, she is feeling better now.

    Besides, I am likely the most boring person you’d ever meet. I’d hate to inflict that on a poor, unsuspecting woman that drove 1,000 miles just to see me. It would be like the unpleasant feeling of being drunk.

    What is so unpleasant about being drunk you may ask? Ask a glass of water.*

    Add to that the fact I’m old enough to be you older brother’s father and it would be a recipe for… “Disaster” might not be a strong enough word. Let’s try unmitigated failure.

    It would be a recipe for unmitigated failure. Hmm, doesn’t quite ring true. It would be a recipe for unmitigated disaster. Better but not quite there.

    Ah! I know. It would be a recipe for Miley Cyrus and Justin Bieber getting married and having children. *shudder*

    So, my Facebook apathy works out best for the both of us. You may thank me later.

    *Blatantly stolen from Douglas Adams’ “Hitchhiker’s Guide to the Galaxy”

    • stubbs says:

      Racing motorized carts sounds like a fun first date; it’s all about the company and doing something memorable!

      I’m glad to hear your wife is feeling better.

  2. Michelle says:

    Okay, this is awesome.

    SInce I’m married, I don’t date..hubs would frown on that…but it’s fun to read about other people’s…

    • stubbs says:

      I hope you enjoy living vicariously through my experiences… perhaps that will make some of them worth having.

  3. This is a fantastic idea! I also have a highly monogamous past, and it’s really excellent to just go on dates with no pressure. I hate first dates, though, they are always so awkward! But, maybe if I went on fifty of them I would be better at it?

    • stubbs says:

      I keep hoping the same thing! We’ll see… I’ve only just begun, so I’ll let you know 50 dates from now if I am any better at the awkward first meet.

  4. greg a says:

    I think over the past few years, I have had more than 50 first dates, and very few 2nd dates. I wish I had the hindsight to write a blog about them. You tend to meet a wide array of characters, some good, some not so good.

    The question is…have you had a 2nd date with any of these?

    • stubbs says:

      I have, but timing can be challenging. It’s slowed down a lot (even first dating) because work started to overtake my life, and then I was busy remodeling, so I haven’t made quite the progress I originally set out to make. It’s definitely turned out to be a much different experience than I thought it was going to be when I started, too. In some ways it’s better than I expected, but it’s also a lot harder [in ways I couldn’t anticipate] than I ever could have imagined.

  5. cath says:

    Hey hey hey…how funny I find your website through the blogess. Then I continue to read purely because your blog is fun only to learn of your 50 first dates project. Ha! many years ago I decided i needed to meet real men. I needed to date. I needed to carve away the crap that had been happening in my life and make men realise that dating was a worthwhile adventure, not a quick path to bed or whatever. My project was ‘6 weeks 6 dates’. the men had to ask me out but my friends and I could jolly them along. they had to pay. they had to be chivalrous and they could not for one second expect anything more than a date. Partway through my experiment, another friend joined in. All the people associated with me, my business, her and her friends chimed in with suggestions. She ended up marrying the first date of her six! Two kids later still happily married. My dating project was sideswiped with the passing of my father…but that didn’t matter in the end. Not too long after I met the man that has become my best friend, and I still credit my dating project with giving me the ability to value myself enough as a datee to deserve the man I married.

    Ugh…dear god i’m a terrible writer!

    What I started out to say, and then sprayed with a whole pile of sentimental crap is…if you have the budget, come to Sydney in Australia, and I’ll do my darndest to find you a pile of first dates here. We have a spare room in our house which you could take advantage of, and there are a million amazing men here that would love to meet someone with your chutzpa.

    my writing doesn’t get better does it? i still sound like a weirdo…just imagine if I was one of your first dates. we’d all be reading about it now…

    thanks for the fun read, i’ll be keeping up with your dating project, and also totally understand if you file me in the loony bin basket and never respond


    • stubbs says:

      I looked at plane tickets from my city to Sydney. Phew! That’s not cheap, is it? I must be on the exact opposite side of the globe. But… if you can scare up 10 Dates Down Under for me (should be easy, what with a million amazing men to choose from, right?) to be compressed into whatever period of time as you think you can handle a crazy blogging couch surfer (so an afternoon of Speed Dating?), then I could probably be talked into making the trip. Oh, and as long as you and your husband aren’t serial killers trying to lure me to my death. That would be so inconvenient for me.

      Your writing is great! I loved it.

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