When she told me she might be pregnant, I knew I had made a big mistake.
Angela called me one evening a few weeks after she decided Andrew really wasn’t her boyfriend. I was still a bit shell shocked by the idea that she was dating my buddy, and now all of a sudden she’s suggesting to me, a guy she barely knows, that she might be pregnant with my buddy’s child. She had to know I would call Andrew, right? (I didn’t.)
For the life of me I can’t figure out why Angela would suggest to Andrew’s friend that she might be pregnant by him. It defies logic, but most good stories defy logic in some way, shape or form.
So why was Angela telling this to me? Let’s back up a bit and remember what life was like in the early days of online dating.
Before eHarmony was a household name there weren’t a billion online dating sites to choose from. If you wanted to scour the Internet for Catholic, Jewish or atheist singles, you didn’t have a specific online destination.
Craig’s List perfected the art of free online classified ads for everything from casual encounters to long-term relationships. But Craig’s List certainly wasn’t the first site helping you find your soul mate via the Internet, sans a monthly membership fee. In the early days of the Internet AOL was king, and it provided plenty of local news, information and services through its Digital City brand. That local service included free online personal ads.
In the spring of 2000 I dabbled with Digital City’s free online ads. Already a skeptic of the personal ad culture, I voyeuristically read the ads from single women in the Twin Cities. I was intrigued by a woman named Susie, and responded to her ad. We chatted by email for a while, yet for reasons I don’t recall, our correspondence ended. She candidly told me about her experiences with the ad she placed, and I eagerly absorbed it. (The one thing I remember specifically, 11 years later, was her description of the outfit she wore on a date. She called it a black FM dress.)
I never met Susie. She was a few years older than me, and a lawyer. She seemed out of my league. I was a 29-year-old working professional, but I wasn’t much more than an older version of a 23-year-old college graduate. I hadn’t matured much during my 20s, even though I’d already suffered heartbreak I never fathomed possible during my college years. (I can’t explain that heartbreak, either, but it was ridiculously stupid in retrospect.)
Back in 2000 we didn’t have cougars. Sure, “American Pie” gave us MILFs, but the cougar lifestyle hadn’t been glorified at that point. Even though I sensed Susie was intrigued by me, I never seriously considered meeting her. (I just tried emailing her via her old AOL address, which I remember to this day. Surprise! She no longer uses it.)
Instead I met Angela. I responded to Angela’s ad. She replied.
We ended up chatting by phone, and I quickly learned that she had started dating Andrew. She never mentioned him by name, but she made it clear that she had started dating a guy she met through her ad. We had a second phone conversation about a week later and she started referring to Andrew as her boyfriend. At this point I wasn’t interested in chatting with her on a regular basis if she thought she was in a committed relationship, so I wished her well and told her to give me a call if things didn’t work out with her new boyfriend.
She called me about a week later. She was having doubts about her boyfriend. He was busy and giving her excuses as to why he couldn’t see her on a regular basis. There was something during the conversation that triggered my spider-sense. I asked a few questions and learned that her boyfriend was a guy named Andrew, living in St. Paul.
My buddy Andrew, the guy I played darts with most Thursday nights, also lived in St. Paul. Andrew and I didn’t know each other that well, we’d met through mutual friends a couple of years prior, but I knew him to be a serial dater who was quick to use the Internet to meet women. And I hated him for it. He’s a good-looking, charismatic guy who did just fine without online personal ads, but as they say, the rich get richer.
I was rather certain Angela was dating my friend. She noted that she had his picture as the wallpaper of her computer. This was 2000, before everyone and their sister had a digital camera. Jpegs weren’t passed around like pitchers of beer at a frat party in those days.
Despite the fact it was unwise for a woman to invite a guy she had never met to her apartment building, she invited me to her new apartment so I could see the picture of Andrew. Sure enough, she was dating my friend. I didn’t know what to tell her. She thought she had a boyfriend after a couple of dates, and I highly doubted it.
I drove home that night wondering how I wound up connecting with a woman who was dating my friend. I took it as a sign that I wasn’t meant for the world of online personal ads. She was the first person I had met through an online ad and what did I get for my effort? One hell of an awkward situation.
Angela invited me to have lunch with her a few weeks later. She decided Andrew wasn’t boyfriend material after all and must have decided I was worth pursuing. Against my better judgment I had lunch with her, but the weirdness of our situation was something I couldn’t overcome. (I did see her one more time, and that triggered an unexpected encounter with a co-worker. Perhaps I’ll share that tale another day.)
I don’t remember where I had left things with Angela when she called me to tell me she might be pregnant, but that was the point where things went from ridiculous to sublime. And no, I don’t think she was ever pregnant with Andrew’s child.
That was my first experience with online dating, way back in 2000. If that wasn’t enough to scare me away then I’m an idiot.
Here I am, 11 years later, writing about relationships, dating and painful memories from my past. I have dabbled with online personal ads over the years, but never seriously. I have had my share of relationships, but once again I am single. I’m 40, tired and more fascinated by people than ever. I plan to share stories and insight from my life, but I also want to share the observations and experiences of my readers. My life is mildly interesting, but yours is probably far more colorful than mine, and I hope to learn about it as I write this periodic column.
And please tell me I’m not the only one to have met an Angela.
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