My Very First Internet Date, or How I Convinced a Stranger to Blindfold Themselves Alone on Their Porch

When I was 29 and single, it began to dawn on me that most of the  men I felt attracted to were unavailable.  29 is a rough age to be single, if you’re of monogamous leanings (which I was.  Am?  Not sure anymore…).  People who like long-term relationships are often partnered up by then, but the first wave of divorces hasn’t yet hit your age group.  It’s like craving fresh berries in winter—you just gotta wait.  Or settle for frozen.  Or old and dried.  Which is what it felt like when I decided to write my first online personal ad.  Frozen and dried berries, here I come.

Two of my coworkers had recently met seemingly wonderful partners by placing ads on Craigslist.  I don’t remember if we knew about Match.com yet in Portland in 2004, but if we did it surely seemed like only rich white people used it (it still sort of feels that way, honestly).  And Craigslist personals were still respectable-ish.  I mean, I wasn’t about to put a picture of myself up there, but a veiled ad seemed safe enough.  And that was how I came to meet Joey, my first internet special-friend.

Nearly 200 men responded to my ad, which I think was pretty typical for women advertising on Craigslist.  Probably still is the case.  I actually responded to them all, because it seemed like the polite thing to do, so it took me a couple of days to get to Joey’s.  His message stood out for its wit, good-spelling, and charm.  Back then I was a sucker for long, smart sounding messages (now I know these are a red flag!), and he let many interesting tidbits drop into his long reply, like that he had a graduate degree in theology and was Italian.  And that he had nearly become a priest but settled for computer programmer instead, and owned a fat cat and played bass in a band.

After I wrote back, a long, drawn-out correspondence began (I don’t do this anymore, for reasons that will soon be obvious).  Joey wanted to meet right away, but I was too nervous.  He said that he had experience with internet dating, and his experience showed him that it wasn’t good to let expectations build too high.  Oh Joey, how wise you were.  I should have listened.  Instead, I insisted that I needed to get to know him a bit through writing before I would meet him.  And so we wrote increasingly long letters to each other for three weeks.  He wanted us to email photos of ourselves to each other, but I declined.  Where was the romance in that, I wondered?  Weren’t we supposed to fall in love with each others’ SOULS??  We described ourselves to each other, and I created two Joeys in my mind: one was the cutest version and the other was the ugliest.  I figured he would be somewhere in between.  I tried to describe myself, and still do, as less attractive than I think I probably am.  I’d rather be rejected before meeting than after, is the truth.  So if someone is willing to accept me the way I look on my period after the holidays, we’re good to go.

Once I was falling in love with Joey through his letters, I decided it was time to meet.  My anxiety around meeting was ridiculously high.  I had so many fears.  What if he saw me first and hid because I was so ugly?  What if I saw him and he was ugly and I had to hurt his feelings? Really, those were my fears.  That one of us would be disappointed, and either I would get hurt or I would hurt him.  In my hopeful mind, we were already a storybook romance.  I mean, just look at our letters!  They were funny and tender and deep.  Only people in love write letters like that, thought my 29-year old silly self.  But we hadn’t met!  How, oh how could we overcome this obstacle of the body?  How Juliet?  How Cathy?  We needed to be able to meet as just our souls, for that is the realm on which love truly exists!!

And so, in an effort to avoid tragedy, I devised some completely bizarre rules for our first meeting:

Rule #1: We must commit to spending THE ENTIRE DAY TOGETHER.  (I first suggested the entire weekend, but he whittled me down to the one day.)  I was realistic that he wouldn’t be the person I had built up in my head, nor I in his, so I wanted us to give ourselves plenty of time to reconcile the ideal with the real.  The plan was we would meet for breakfast, then spend the day meandering around Portland doing whatever we wanted, and conclude with dinner.

Rule #2: To avoid the conundrum of one of us seeing the other first (wtf? I was so scared, obviously), I would drive to Joey’s house where he would be waiting for me ON HIS PORCH WITH A BLINDFOLD AROUND HIS EYES.  I kid you not, these were my terms, and he actually agreed.  I would get a chance to look at him, one-sidedly.  When I was ready, I would instruct him to close his eyes and then I’d remove the blindfold, put it on myself, and instruct him to open his eyes.  He could then look at me, and then he’d remove the blindfold and… we’d run off into the sunrise with bluebirds and hearts and rainbows, or something like that.

The morning arrived.  I was giddy with excitement.  I’d read through our long exchange of romantic letters the night before, and picked out the perfect outfit.  Joey lived in the opposite quadrant of the city, so I made sure to give myself enough time to drive there.  It was a Saturday morning.  The streets were quiet.  I was waiting at a red light to get on the bridge over the river.  The light turned green, I accelerated, and in a flash the car next to me slammed into me as another driver ran his red light and plowed into her car.  A 3-car accident in the middle of the intersection.  Nobody was hurt, so I drove my hobbled car to the side of the road and exchanged insurance information with the other drivers as quickly as possible.  Minutes were ticking by, and on the other side of the city, Joey was sitting on his porch, blindfolded.

Ten minutes later, I continued on my way.  The newly smashed right fender of my car made a grinding sound against the tire.  I arrived at Joey’s about 15 minutes late.  I didn’t expect him to be waiting, but there he was, on his little stoop, kneeling and blindfolded as though waiting to be executed.  He lived in a courtyard style apartment, so he was in full view of all his neighbors.  I rushed up, out of breath, and apologized for being late.  Immediate disappoint washed over me.  He was not at all what I was hoping for, even on my low end of expectations.  It’s not that he was unattractive, it’s just that I knew, on that language-less cellular level, that I wasn’t attracted to him.  I assessed my feelings, fixed my expression, and told him I was ready to remove the blindfold.  So we did our whole thing, and he looked at me and told me I was beautiful, and then the blindfold came off and we went inside.

It wasn’t a bad day.  I still had these feelings of falling in love with him.  So I spent the day doing exactly what I had planned on doing, which was trying to love his physical self as much as I’d come to love his cerebral self.  But the thing about writing letters, that I’ve come to learn, is that you really get so little of a person through their writing.  Especially if they’re a good writer, which he was.  Probably the weirdest part of the day came in the evening, as we were walking to dinner.  We had eaten at a dive bar for breakfast, at his suggestion, talked at his apartment, made out, rested on his bed, snacked for lunch, and walked around the neighborhood.  Now we were walking to a nearby Italian restaurant and a couple was walking towards us on the sidewalk.  Just before they reached us, Joey suddenly stopped in his tracks, turned, knelt down on one knee, and bowed his head.  The couple, startled, stepped around him.

I had never seen anybody genuflect outside of a church, so I didn’t know what he was doing.  I looked around, and then saw that there was a small garden tucked off the sidewalk with a large statue of Jesus on the cross.  I realized we must be behind a church or something.  For several long minutes Joey didn’t say anything, but stayed frozen in his prayerful pose.  I stood there awkwardly.  Then he got up and resumed walking.  He started talking about the restaurant we were going to, and so we just pretended that nothing unusual had happened.  During our mediocre Italian meal, I asked him about the kneeling.  I think I said, “What was that?”  He replied, “Oh, I always do that there.”

Joey and I lasted a couple weeks.  I learned that he smoked a lot of pot, which is a turnoff for me.  He had an annoying habit of stopping at every single cat in the world and playing with it for minutes on end, which made every neighborhood walk take forever.  He also talked A LOT, and tended to hold his fork midair with food on it while he talked on and on.  I would grow increasingly anxious about the uneaten food dangling in the air.  Oh, and he genuflected all over the place.  But really, those are all things that I could have found terribly endearing if I had truly loved him.  But I didn’t, for mysterious reasons.  And so I ended things with Joey over the phone one day.

I realized that it had taken me two full weeks and about 6 dates (including our long day together) to get to know Joey enough to realize that I wasn’t into him.  The problem was, if we hadn’t written those long letters and “gotten to know each other first”,  Joey wouldn’t have gone past one or two dates with me.  Building him up before meeting him had been a disastrous idea, and had led to him getting hurt in the end.  So I decided that internet dating sucked and I wouldn’t do it again.  A promise that came undone 18-months later thanks to a super cute 20-year old boy in a tutu that I met on a naked bike ride.  But that’s another story…

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