This story has been making the rounds for years, at least among my friends (both IRL and online). I’ve been hesitant to post it on my blog because it contains “adult themes” and, well, hi, mom! But I’ve been listening to a podcast called Risk! lately, and its tagline is “true tales boldly told.” This has given me the courage to finally come clean and share my story. It’s a doozy, but is nowhere near as bad as some of the stories on Risk!. Because I do have family reading my blog I feel some obligation to be a little discrete, so I am substituting the euphemism “managing her stock portfolio” to keep this in PG-13 rated territory.
This is the story of my first date in 20 years, and it takes place in 2006. It’s on the long side, but trust me – it’s entertaining. And every word is true.
In November of that year, I was separated from the woman I had been married to for 14 years. We had been high school sweethearts, but had been separated about two months, had each purchased townhouses, and our divorce was taking place in a few weeks. It was time to explore the dating world, only I was scared to death. At the ripe old age of 37, I felt like a fish out of water. I was not into the bar scene and didn’t have any friends or coworkers attractive enough (or single enough) to date, so naturally I turned to the Internet.
Popular sites like Match.com and eHarmony cost money and I personally do not believe one can put a price on love…okay, that’s bullshit. I was really just a cheap bastard. In any case, OK Cupid was getting a lot of attention and it was free, so I created an account, posted an online profile, and sat back to see what would happen.
A woman named Jennifer happened. She read my profile, messaged me and said I was “cute.” Game on, baby.
I had no idea what the dating rules because the last time I had been out with somebody new, Mr. Mister was all the rage. I was definitely surprised by how forward Jennifer was. She was quite the aggressor, and boasted that she managed her stock portfolio really well. I asked her how she could be sure, and she replied, “One guy went into a seizure when I finished. And he wasn’t even epileptic.”
Naturally, I was intrigued. My own stock portfolio had not been managed in quite some time, so we arranged to meet up. Taking the advice of a friend, we decided to get together at a Starbucks in the mall. It was a public location and would make for a short, no-obligation date if things went south. The evening of our date was rainy. Very rainy, even by our already-soggy standards Pacific Northwest standards. Keep this in mind, because it’s important later.
Right off the bat, things started going wrong. I should’ve called the whole thing off right then and there, but I was curious to see whether the Dow Jones would close up that day, so I didn’t bail. We had agreed to meet at 7:00, and because the mall was just a few miles away, I hit the road at 6:40, allowing myself some extra time since it was dark and pouring rain and, truth be told, I was looking forward to meeting her. The concept of dating was both terrifying and exciting, and I was ready to plunge in. The minute I arrived, she texted me, letting me know she was stuck in traffic and running late, so could we make it 8:00 instead? I was already standing outside The Gap and didn’t want to go back home only to have to navigate through the autumn storm all over again in another hour, so I decided to kill time by wandering the mall instead. This made me feel awkward, because it was a Friday evening and the place was teeming with packs of teenagers. Being the older guy in their midst shuffling past Bath & Body Works and Cinnabon while they goofed off just felt weird. Finally, mercifully, Jen texted me letting me know she had arrived, so I made my way to Starbucks.
“So, have I aged much?” were the first words out of my date’s mouth when she pulled up a chair beside me.
Has the Colosseum aged much?! I was tempted to reply, but bit my tongue instead. Her online profile had included a photo, but she had warned me in advance it was ten years old. I don’t know why that didn’t set off any warning bells, but remember, I was brand new to dating and a little naïve. In reality, her photo was probably twenty years old. The girl on my monitor had been fresh-faced and reasonably pretty, but the one staring back at me now had a face so wrinkled it resembled a roadmap. Destination? Old Town. I was learning – on the fly – the Rules of Dating in the 21st Century.
Rule #1: Make sure you have a current picture of your date.
As she leaned in close, I caught a whiff of her scent. Perfume? Nope – cigarettes. She reeked of tobacco smoke, which was a major turn-off. Under the word Smokes? on her profile, she had written N/A. Apparently, that meant Nicotine Addict.
Rule #2: Learn all you can about your date’s personal habits beforehand.
By now I had to fight off the instinct to bolt for the nearest exit, but Jen had just spent 90 minutes on the road driving through a torrential downpour, so I figured I owed her an hour of my time. Plus, she had paid for our drinks. I’m not even sure how that happened but I’m all for women’s lib, so I didn’t put up too much of a fight. I prayed instead that my phone would ring and I could fake an emergency.
Rule #3: Always have an escape plan.
Our initial topic of conversation? The fact that she had lost 300 pounds. Honestly, she looked like she had another 200 to go. I have nothing against women with a little meat on their bones, but when Jen mentioned that she’d contemplated buying an electric wheelchair to get around, I think I recoiled in horror. Attempting to steer the conversation toward more comfortable territory, I asked her where she lived, expecting to hear something like “an apartment” or “Taylor Street.” Instead, she replied, “with my parents.”
Rule #4: Find out your date’s living arrangements before meeting up. Anybody still shacking up with their parents when they’re pushing 40 has issues.
She told me about her 21-year old son and 14-year old daughter, all living together under one roof with her folks. To make matters worse, she dropped another bomb by informing me that she was a grandmother, delivering this blow with what sounded like pride. I was in my 30s and had no desire to date a grandma! Suddenly, she was rolling up her pant leg. Why? What was happening now?? OK, she was just showing me her tattoo. No big deal. I like tattoos. But this was no tiny butterfly on the ankle; it was a sprawling dragon tattoo that wound around most of her leg (which was quite ample to begin with). I’d had enough, so I tried to courteously wrap things up with some half-baked excuse about getting up early the next day, never mind that it was Saturday. Ever the polite guy, I walked my date – this chain-smoking, obese, heavily wrinkled, tattoo-sporting, still-sponging-off-her-parents grandma – to her car.
Only, her car was nowhere to be found.
We scoured the parking lot for what felt like an eternity, getting drenched thanks to this deluge of epic proportions, searching for a car that wasn’t there. “Oh, shit,” she kept saying, over and over again, a broken record. Oh, shit, I kept thinking. I envisioned a long, wet, cold night spent talking to the police and filling out paperwork. I’d be obligated to drive her home, too. To her parents’ house.
“Are you sure you didn’t park on the other side of Macy’s?” I asked.
“Oh,” she said in response. “There’s another side of Macy’s?”
Of course, this was exactly what she had done. But I wasn’t angry; instead, relief washed over me as we finally located her car, which happened to be a purple Trans-Am I’m pretty sure you could have spotted from the moon. She offered to drive me to the other side of the mall “so you won’t get wet,” which was laughable considering I was already soaked to the bone, but again, I’m a polite guy so I hopped in. When we got to my car I thanked her for the fun evening (I am apparently also a liar), gave her a quick hug, told her we should keep in touch, and took off.
Ten minutes later, she was texting me.
Is it just me, or is a hug and “keep in touch” the kiss of death?
Overly dramatic much? I politely responded that I’d enjoyed the conversation but hadn’t felt a connection. And straight up asked if she’d been hoping for a goodnight kiss.
When a person says she doesn’t have to work the next day, Jen responded, it means she could have kept you up VERY LATE.
Reading those words, I nearly swerved off the wet road. The text was accompanied by a little smiley face emoticon with devil’s horns, making the implication clear. This self-professed stock portfolio expert would have managed my stocks and bonds all night long if I’d given her the chance, and probably would have diversified my holdings while she was at it.
I figured I was more content keeping my money under the mattress instead (these analogies are getting weirder by the minute), and bid her adieu. Aside from a quick email exchange the day before Thanksgiving, I never heard from Jen again. Soon after, I deleted my OK Cupid profile. Within a couple of months, I began dating a woman who was both childless and grandchild-less, and completely free of tattoos. Whew! Right?
Wrong. She was batshit crazy. And married. And faked two pregnancies just so I would stick around.
But that’s another story…