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The Women I’ve Loved

Posted on May 28, 2020August 2, 2022 by Steve Ainslie

Pam was my first love. When I met her in our high school Spanish class, I could tell she liked me. She smiled a lot and never stopped talking to me. Being a sophomore, I remember thinking sarcastically, “Oh great, a freshman has a crush on me!”

She was cute with big blue eyes, blond hair and a big smile. It was only a few weeks later that I asked her to go to the movies. I don’t remember the movie at all. I remember we kissed the entire time. By the time the movie was over, I was in love.

We walked home from school together everyday. We hung out and made out as much as possible. We babysat her sister, went ice skating, went to the  movies and even talked about marriage some day.

Thing went great right up until she dumped me.

“I hate you and never want to talk to you again!” she yelled and then hung up on me*.  That, my friends, was how Pam blindsided me and broke my heart way back during the dark ages.

I had no clue it was coming. We had spent time together that very same day at school and then walked home holding hands that afternoon. We had plans to go the movies a few days later. We were laughing, kissing and enjoying our time together.

And then later that evening “blam” – I never even knew what hit me.

*Pam contacted me decades later because she still felt guilty about this. She told me her mother made her break-up with me because her mother didn’t approve of my stepfather. It made me laugh because I didn’t approve of him either! 


I dated a bunch of girls over the next two years.

  • Holly, who I met at a CYO dance was sweet and tender. But after a few dates, I broke it off because she seemed too innocent. Years later, Holly was the committed girlfriend of a good friend of mine. I think they eventually married. 
  • Denise was my friend’s sister, who I escorted to her semi-formal dance as a favor to her brother. We went on two dates before I ended it because her mother made Denise call her every 30 minutes to check in because she didn’t want her messing around. Apparently, this didn’t work because Denise got pregnant before graduating high school.
  • Lisa was an 11th grader and went out with me a few times when I was in 10th grade. She was super-hot and reminded me of Bo Derek. I wasn’t in love with Lisa, but could easily have been. One night when we were fooling around while she was babysitting, I tried to tell her I was falling in love with her. She made it clear she wasn’t interested in my protestations of love and that she planned to date other people. I was so discouraged, I never went out with her out again.
  • Tammy. Of all the women I dated, Tammy might have been the absolute sweetest. I met her when I picked up her friend from dance class one Saturday afternoon. Tammy came from a good family – in fact her cousins pulled me aside before our first date to tell me I’d better never hurt her. Tammy was fun, athletic and completely well balanced. I broke up with her after a month because I though I would ruin her. She was too innocent to be with someone like me. Years later, I worked one summer with one of the sweetest men I had ever known. One night, his girlfriend came to pick him up and it was Tammy! They married and are still together 30 years later. 
  • The One Offs. Those were girls I dated a few times before we realized it wasn’t a good fit. The high school swim team champion. The American Indian. My other friend’s sister who towered over me and spent our date telling me how she could out lift me in the gym. The brunette I met in line outside the under 21 dance club. The girl from the Gateway Clipper. The lifeguard. The Tai Kwan Do expert. The piano player. The girl who gave her number to another  guy at the Dirty O while we were on our date!
  • Julie, who I met at the Hawaiian Party my friends and I cooked up one cold  February night as an excuse to dance with girls in bikinis. Julie was my rebound girl after Pam. I fell hard in lust with her. She was a fabulous kisser and we had fun fooling around. Otherwise, we were a horrible match. She liked Madonna, I liked Pink Floyd. She played basketball, I went to work. She lived in the suburbs with her perfect little family. I despised her fat bitch mother and her wuss father and they hated me – the rebel hippie with a beard and earring. By the time we broke up, ironically at a Hawaiian party that Julie held a few months later, I knew we never had a chance. Julie next dated some goober from her high school and married him.
  • Jenny, came after Kerrie below but I’m putting her here because we had a short lived summer fling. Jenny was one of my junior lifeguards when I ran the pool. She had a big grin and long skinny legs. I thought she was kind of cute and I knew she admired me. She was super sweet too. But she was 18 going to college and I was 20 on my way to dropping out. We broke up after she went away to college. Jenny was a genius who had a full academic scholarship. I  always figured she’d go far in life but have never tracked her down. 

Kerrie was my second love.  I met Kerrie when I was 17 and was trying to date her sister.

Her sister’s boyfriend was leaving that summer to join the army and I was trying to convince her to dump him so she could date me. She laughed me off. During my attempted courtship I went to her softball games where I met her kid sister Kerrie. I tried to setup Kerrie with my friend, so we could double date and instead we ended up up dating each other.

Kerrie and I were a great fit. We were dirt poor but ok with that. I thought I was way smarter than she was (of course I though I was smarter than everyone I met), but it turned out she was quite intelligent – but not street smart.

She was 2 years younger than me so I was her first boyfriend. We had a lot of fun together. We played tennis. We hiked. We went to the movies and ate calzones. We would go to the drive-in, lay on the hood of the car making out, watching shooting stars and eating a bag of soft batch cookies. I taught her to drive. She made me laugh. We wrote each other love letters every morning at school.

Kerrie and I had a rule that worked great for us – we dated every other night. If we saw each other every night, we were at each other’s throats. The every other night schedule gave us time to work, hang out with friends and do other stuff apart.

Kerrie was a real athlete. She was an all-star softball player and joined the tennis team as a walk-on in high school. She was a total jock. Kerrie taught me to play. I taught her to drive. We were committed to each other and in love.

We stayed together for nearly four years. It was only after I was a college sophomore that I realized we’d drifted too far apart. I broke up with her because I realized we no longer loved each other and I didn’t want us to grow to hate each other. I saw Kerrie once on the bus a year later but never heard from her again. I googled her a few years ago. She became a successful IT analyst and had married. I hope she is happy and remembers our time together as fondly as I do.


Ellen was my third love. I wrote about how I met her here and have written much more about her throughout this blog.

We weren’t supposed to work. Ellen was 19 years older than me. She came from money, I came from poverty. She was Jewish. I was Catholic. She was classy. I was poor white trash. She smoked. I was a health nut. She had 2 kids and was getting a divorce. I was 21 and had just dropped out of college. I wanted to date a woman and have a family. She wanted to have fun.

We were together for 29 years until the day she died.


When I was younger, I thought love was a once-in-a-lifetime occurrence that happened with a one-in-a million partner. 

When I got older, I realized that Ellen and I weren’t  one in a million. We were coworkers. We were attracted to one another. We were one-in-a-hundred at most. But that was enough.


I wonder if I’ll ever love another woman again. I always knew I’d never love another woman the way I loved Ellen. Writing this post made me realize that I’ll never love another woman the way I loved anyone before.  Because I’m not the same man I used to be and that’s not the way life works.

Today, I have no interest in getting married again. I don’t want to raise children again. I have no desire to move backward. I might never consider a full-time, live-in romance again.

I tell my friend I want a woman who wants to walk the dogs together, eat dinner, f**k and then go home to her own house.*

My friend tells me I need to come up with a better pitch if I intend to snag a woman.

But I’m not at all concerned. I’ll never do online dating and for now, I’m content to be alone.**

It’s been a long time since I’ve dated someone new. Eventually, I’m sure I’ll date again. As for falling in love, only time will tell.


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