How to meet cute boys – dating in the 90’s

I’m writing this at 10:30 pm but you’ll see the post in the morning. I need to get back to scheduling daily posts. I also really need to try and get some regular sleep going on here. But a question on Twitter reminded me of a story that I haven’t shared here yet. It reminded me of how carefree I used to be when I was younger – and much thinner. And “perkier” – you know how things go with gravity as you age.

It was the late 90’s and I was out of high school. My family didn’t have money for me to go to college and I didn’t have the grades. I also had no clue what I wanted to do for education. It’s my biggest regret. I wish I had gone into business and at least got a business degree. Hindsight really is 20/20.

Instead my parents said I needed to get a job or I had to move out. I guess at 19 it was a fair deal. And so, I hit the pavement. Quite literally. We didn’t have big job boards like Indeed or LinkedIn back in those days. We relied on newspaper ads, window signs in businesses and word of mouth advertising. That’s how I got most of my jobs in my youth.

I went to an interview one night – the ad had said it was an office job answering phones and making calls. Little did I know back then – that was “code” for cold-calling. I was told to sit down at a desk that had a single phone on it. One of those old office phones like in The Wolf of Wall Street. I’m really dating myself here. There was a book on the top of the desk. A cup with pencils. And an empty chair next to me. I remember glancing around the room. There were a handful of people there still wearing their winter jackets. It was freezing in the room.

Just before the “interview” was to start, a guy close to my age swooped into the room and sat in the empty chair next to me. “You know what this is about?” he said as he nervously pointed to the thick book in front of us. I shook my head and said, “I think we’ve been duped.”

Sure enough, the “interviewer” went on about how we were going to practice the script – ah, so that’s what the book was. It was a script. We were going to call people and try and sell – whatever product they were pushing. It might have been a vacuum. Could have also have been some kind of furnace cleaning service. I honestly don’t remember. In fact now that I try and think about it – I don’t remember much of the night at all.

About ten minutes into the “interview” the guy next to me whispered, “You want to get out of here and grab a beer?” I looked up at him in surprise. Sure, he was cute enough. I’m ashamed to admit I don’t even remember his name. Or what he looked like. I’m guessing it was blonde hair and blue eyes though. I was a sucker for the blondes back in my day.

We pushed back our chairs which scraped loudly on the cold floor. I remember that because everyone stopped talking and stared at us. We were all cool like as we grabbed our jackets and walked out.

I think we must have gone to play some pool and had some beers. I don’t think anything came out of it because I don’t remember seeing the guy again. That’s how I was back then. I never considered myself hot. I’ve always been chubby or overweight. But – yet, I somehow got dates all the time.

Like – ALL the time.

Like when I met Steve, the trucker at a Husky truck stop – that same summer. I got lost on the way to another interview. But that’s a story for another day.

All I know is that back then – life seemed simpler. We made the best with what we had. Getting around on the bus seemed like second nature compared to now. Maybe it’s because the city was much smaller back then. Less people to deal with. Less congestion. Less noise in general.

Maybe it’s because we didn’t have cell phones or social media to distract us. We actually had to put in effort to meet someone.

There was one guy I dated casually for a couple of months. I don’t even remember his name and this makes me feel so guilty. I think I can blame that on aging. This was over twenty years ago. No, nearly 30 years. God, really? Am I that old now?

But this guy was so amazingly sweet. He would cook me dinners. He bought me “friendship” roses one day when I was in a rough spot. And then again for Valentine’s Day. Doug, I think. Maybe his name was Doug. I remember the letters. We used to write the most romantic letters. That’s definitely a thing of the past. Do people even write letters anymore? Or is it all communication by text and email?

Reminiscing about the good old days always makes me feel nostalgic. Friends keep telling me I should write a book about my experiences. But then that would mean admitting to a lot of terrible things I did as a young and naïve teenager.

But do remember to ask me about Rob – the guy who stalked me for three months and proposed to me over the phone. Because that’s a story you don’t want to miss.

It’s a good thing we didn’t really have blogs like this back then. My daily entries may have sounded like old Penthouse letters. “Dear Penthouse tonight Dave and I …”

Oh yeah. Dave! The super jealous guy who would call all hours of the night if I was out with my roommates. That was around the same time as Rob. It’s all coming back to me in a flood of memories.

I picked up guys without even trying in the oddest places. The pool halls. Job interviews. A Husky truck stop. And then there was the time when I on a date with a guy and his brother Peter. I actually danced and had drinks with two brothers. And I didn’t even feel bad about it. Although I feel a twinge of guilt now.

But weren’t we all a little dumb and naïve at 19? Or was it just me?

I miss those days. When life was less complicated and I was more carefree. Wouldn’t it be glorious if we could revisit our youth? There are so many things I’d have done differently. And yet, I know some things would have remained exactly the same.

I’m going to leave with you this earworm. You’re welcome.


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2 Comments Add yours

  1. Haha we must be the same age because I remember everything the way you do and I finished highschool in the 90’s too. We were around before the internet! Hahahah now I DO feel old. I loved those times of circling ads in the newspaper and ‘literally hitting the pavement’ as you say. I loved that we had to LOOK at each other back then, LISTEN to each other. There were no dates or filters, if you saw a cute guy in the street/cafe/whatever (what is with you and truck stops?!? Hahaha) then you really saw him. You didn’t see his doctored image. I’m loving that you picked guys up so easily, that must have been so much fun.

    Please tell me about Rob!

  2. Wendy says:

    Haha I think we are too. The 90’s were such a different time compared to now. I’m so glad that we didn’t have social media as a kid. I can’t image what it’s like growing up with all this technology now. It seemed much easier to meet people and keep relationships going back then!

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