PW's Most Awkward Date Ever (So Far)

Before I begin this post, there are a few things you should probably know about me.  They may seem off-topic, but it is relevant to the Most Awkward Dinner Date I Ever Went On.

I'm firmly in the liberal/progressive camp when it comes to both my politics and how I live my personal life.  I have been for most of my life.  It matches my moral compass the most closely and I couldn't conceive of living any other way.  I vote either Green Party or New DemocraticParty, depending on the election, what's at stake and the candidates involved.  Most conservatives (at least nowadays) would sneer at me for being a 'socialist' (little realizing, of course we are ALL socialists, just to varying degrees).  Now having said that, I believe that most people who identify as conservative are, at their core, good people.  While I don't necessarily agree with conservatives on most topics, I believe in their sincerity of doing what they think it right.  I can respect that, except when it comes to a few things.  Specifically when it comes to issues of race, gender or orientation.

Part of my journey as person is coming to terms with and overcoming my own racism, sexism and homophobia.  I am all these things.  No, I'm not saying this to assuage my white male liberal guilt.  I'm merely stating facts.  Being racist, sexist or a homophobe, or putting up with these things in my daily life won't get any of us anywhere.  Pushing other people down merely gives me the illusion of being elevated above them.  It doesn't actually make it so.  If my neighbour doesn't have the same rights, opportunities and harassment-free environments I do, it affects me.  I take this shit seriously.

Having said all of that, there are times I don't live up to my own morality.  It happens.  Often someone makes a racist comment or a gay joke and I pretend I didn't hear it because it's easier.  Or I don't want to rock the boat.  Or whatever.  I do what I can, but I'm not perfect and there are many times I've lacked the courage to take a stand.  There have been times I had, there have been many more times I haven't.  Now that I'm a father, I do voice my opinion more as an example for them to follow.

Soooo anyway, about this date...

It is 1995.  I'm 19, fresh-faced and fancy free living on my own out west.  I left home, the city and the province abruptly a few weeks after my high school graduation at the age of 17 and it would be about 3 years before I'd be back in Winnipeg.  That is a long and complicated story for another day.  Anyway, I was working as a gas station clerk, living in a cheap apartment above an appliance repair shop, partying almost constantly.  Things were okay... I was living mostly for the moment, the way 19 year olds often do.  Happy memories, but something I wouldn't want to revisit.

I was beginning to really grow into my own as far as sex and relationships go, which was a far cry from being an introverted nerdish bookworm in high school.  I was experimenting a little with same-sex relationships, but while it was fun, it really wasn't my cup of tea.  For the first time in my life, I was happy with how I looked.  I looked like the love child of Matthew Sweet and Gord Downie and dressed like Kurt Cobain on the MTV Unplugged concert a year and a half earlier.  There were quite a few partners that came and went in that stretch of time.

Anyway, in the middle of all this chaos, I was at a local bar one night with my cousin who was in town visiting at the time.  He happen to know a woman who was sitting with a couple of friends at the table next to us.  She was a native Winnipeger as well.  We started chatting and hit it off almost instantly.  Her name was Enid (so dubbed because we danced to the Barenaked Ladies song of the same name that night).  We talked and laughed and danced and talked and laughed some more.  I noticed after a while I was holding her hand without realizing it.  She was absolutely beautiful.  She looked like a 21 year old Nana Mouskouri with reddish-blond hair.  An absolute stunner.  Just my visual type.

The end of the night approached and she invited me back to her place.  I would have run there if she told me to.  We got there, but her sister/roommate was up watching television.  We went into her bedroom and made out for an hour or so but she wasn't comfortable going any further.  That was disappointing, but okay with me and I ended up sleeping on the couch that night.  I left in the morning with the promise we'd see each other again.

And we did.  We went out for coffee for a couple of hours and chatted, mostly about our time in Winnipeg (it turns out she grew up in the same end of town I did, but went to the 'other' high school.)  She was open about the fact she found me really attractive, and liked my personality, but wanted to wait a bit before getting physical.  I wasn't thrilled about waiting (I was 19, after all), but I was really attracted to her as well, so I could deal with that.  We went back to my place, watched a movie, made out some more and she went home.  We made another date that weekend.  I decided on dinner at a local Italian place that I heard was pretty good.

We talked on the phone every day until the date.  We chatted, but there was a bit of unease beginning to creep in.  She talked about her ex-boyfriend.  A lot.  Especially about the sex they used to have.  I'm not a jealous person by nature, and I wasn't jealous here (well, maybe a touch), but I was left kind of annoyed by it.  To me, it seemed a trifle rude and it sounded like she was probing me a little, looking to see if I sounded jealous or otherwise trying to get a reaction out of me.  It was getting to be a real turn-off, but we had such a strong connection before, I willing to let it slide for the time being, and I'd just politely tell her to cool it if it kept coming up.

Anyway, it's date night and she walks in, looking absolutely radiant.  We take our seats, have a glass of wine and continue chatting.  Things are going generally pretty good, but was still bringing up her ex-boyfriend every other sentence.  Finally I had to ask her nicely if we could stop talking about the ex so much.  She agreed, apologized and we talked about a few other things before the conversation slipped back to the ex again.  I was about to say something again when she dropped this little gem:

"Oh yeah, my ex called last night - we talked a bit and then we had phone sex... it was silly and I just did it 'cause I was bored."

Okay, there was a little build up to this that I didn't explicitly mention.  I don't exactly remember what it was, it was 17 years ago after all, so she didn't exactly drop this bomb entirely unannounced. 

But still... really? 

I sat in silence for a moment digesting this little tidbit.  I was irritated, but it really didn't strike me yet what exactly she said - it was just so gauche and inappropriate for a date I was really caught for something to say.  I mean, if she's still doing that with an ex-boyfriend... okay.  It's not like we're an item or anything... but why be so explicit?  And couple that with her affirmation that she is not going to do anything physical with me yet and I was at a bit of a loss.  I was trying to come up with something that was diplomatic and expressed my annoyance.  While that was going on, she literally dropped this bomb out of the blue.

"I really like you Wanderer, and I want to go out with you, but I'm not going to have sex with you."

If that happened today, I probably just would have thanked her for her time and walked out on the spot.  At the time, I had next to no formal dating experience.  I was still kind of thinking she was winding me up and she would be laughing any second.  It's not like I was overly aggressive or anything - our make out sessions were pretty steamy, but she had her boundaries and while I tested them a bit, I respected them.  And I didn't feel I was too aloof either, at least going by those same make out sessions.  We came as close to the border between what they would have called 'heavy petting' and sexual acts as I believe two people could go.  And we were both in it with gusto.

I seem to remember myself asking  "So what exactly are we right now?  Dating?  Friends?  I'm not sure and I'm not sure what to think about what you're telling me.  It seems to me like you want to have sex with your ex while keeping me in your back pocket in case things don't pan out, AND you want me to be cool with all of that.  I like you too, and I'm reaaally attracted to you Enid, but I don't do that.  You're with me or you aren't.  If you're with me, great.  If you're not, I can respect your decision.  But no half-assed 'sleep with him/date me platonically stuff, okay?"

Wow, you're all saying to yourselves.  That's pretty awkward.  Yes it was.  But IT GETS WORSE.  A whooooole lot worse.

She asked if we could finish our date and she promised she would think about what I had to say and give me a real answer about her intentions tomorrow.  That was fine with me, but I had a strong feeling things weren't going to work out between us.  And with the rest of our date, that feeling cemented itself.

We talked more about this and that, and she made some kind of compliment about me being mature for my age and not immediately trying to get into her pants.  I shrugged and thanked her, and then she dropped the Hiroshima of bombshells on me.

"That's what I hate about blacks.  If I'm out at a bar or something, they're ALWAYS trying to get me into bed.  There was this nigger in high school, and I used to call him nigger all the time and it used to drive him nuts!  It was so funny, and I got away with it too.  All they think about is sex.  I can't stand black guys!"

I'm abridging this tirade greatly, and I can tell you that she dropped the n-bomb a lot more than that.  You know how in movies, a character will say something really inappropriate and you hear that record-scratching sound effect and everyone in the room will collectively gasp and look at the character like he's completely crazy.  Well, this is how I remember this incident.  There were nine other tables and their conversations went deafeningly silent.  I could feel everyone’s eyes on me.  My face turned beet red.

Look at him, I imagine they’re whispering to each other, clucking their tongues and shaking their heads.  He wants to put his dick in a RACIST.  For SHAAAAMME!!

There is no doubt that everyone heard her.  I desperately wanted to say something, but I was so fundamentally shocked, all I could muster was “I have to use the washroom.”  I went and stared at the mirror for a while.  What the hell do I say to something like that?  Was she serious?  Was she trying to push me away?  What the fuck?  I washed my hands and slipped out of the restaurant and went home.  Cowardly?  Probably.  But I was baffled and reeling and had no real desire to go back and confront that dining room, even though I knew I had done nothing wrong.  I didn’t call her.

She called a couple of days later.  She asked if it was the racist language she used that I left, and I said it was that and her talking about sex with her ex-boyfriend that kind of killed my desire for her.  She said she was sorry, but she ‘had some personal problems’ she was working out (she didn’t elaborate and I didn’t ask).  She asked if we could try again, and I said no, that dating someone who holds such narrowly racist assertions wouldn’t be possible.  At that, I wished her luck and hung up the phone.  I was still pretty upset, because although I didn’t paint a flattering picture of her here, Enid had a whole host of really good qualities.  She was intelligent, (usually) kind, fun, nerdy, cute, and had excellent taste.

Oddly enough, she called me a few years later out of the blue when I moved back to Winnipeg.  Don’t know how she got a hold of me, but she was back in the city herself and we chatted for a while, mostly about jobs mutual people we know etc.  I was about ready to hang up, when she asked if I wanted to hook up.  No dating, no anything, just sex.  I’m ashamed to say I was tempted, but turned her down as I was dating someone else.  Even if I was single, the drama associated with her would probably(?) been enough to put me off.  In the end, no matter how hot, racism is just a gigantic turn-off.

So now I’m ‘in the dating scene’ again, and I absolutely hate it, but I’m somewhat comforted by the fact that no matter how awkward a date goes, it probably will never get that awkward.

How about all of you?  What’s your most awkward dating experience?




In a funny way, here's to Enid, who if nothing else provided a good story to tell...