The following are highlights from my 2023 online dating travails, in my late 50s. These two stories cover numbers eleven and twelve of over twenty encounters.
Mattress Shopper
One of my precious few “organic” dates (non-dating app) came into the store one lazy evening. Nothing moved me about Maria, probably in her late 40s, until she began entering sleep details into our “BedMatch” computer, which allegedly provides the best mattress options for each customer. With Maria’s back to the store, I became smitten. Let’s just say every other superficial feature can be average if a woman has a booty like hers. Holy Jesus.
I kept it all business to start with, taking her to recommended mattresses and discussing their various features. I also gave thanks that I’m pushing sixty. Otherwise, I would’ve worried about tamping down a boner the whole time. Such a transgression might send a solo woman out the door post haste.
Maria knew exactly what she was working with, too. She swung her hips around when simulating sleep positions and exaggeratedly presented her booty in the process. (Or maybe there was no downplaying that thang no matter what she did.)
For the record, I go out of my way to be respectful to women trying out beds in the store. I never leer and avert my eyes no matter how badly I want to look. When they’re lying on their sides, I scramble to where the woman can see me. Maria seemed to realize this and kept flipping abruptly, seemingly forcing me to check out her backside. I eventually obliged her, slowing down and taking it all in, accepting the come-on.
We chatted about this and that while sparks flew, and I came closer and closer to asking her out. I paused only due to the debacle described in Part Four of this series, i.e. hitting on a customer could be seen as staker-ish. However, this case was “safer.” Maria was in my age bracket, and she hadn’t purchased a bed yet, so I didn’t have her number or address. Still, once bitten, twice shy. I finally threw out caution when Maria playfully mocked me for not asking her out yet. I did so, and I’ve never been less bothered by a customer leaving without buying.
Our first date came a couple of days later, back when West Asheville’s Sunny Point Cafe still served scrumptious dinners. I soon noticed Maria wasn’t as attractive when I couldn’t catch an eyeful of her ass every thirty seconds. She seemed nervous initially, running short of breath. She became more relaxed as the wine flowed and the meal progressed, making me feel better too. Soon after we wrapped up the meal and moved on I made a crucial error.
I planned to patronize a tavern along eclectic Haywood Road on a lovely evening. To grab a beer at the bar and get closer to Maria than across a table. She seemed lukewarm on the idea because she didn’t want more to drink. “But I’ll watch you have a beer,” she offered. While polite of her, I nixed that idea.
I should’ve suggested sitting on a sidewalk bench to people-watch and even passed by an empty one without sitting down. I figured walking to her car would be more comfortable, and we’d plan part two of the evening there. Or just talk and make out. Maria got kind of handsy around this time, after all.
We strolled to Maria’s car, which at first appeared to be on a quiet side street. Alas, the road proved somewhat busy, which made conversation and comfort difficult. Worse, like an idiot, I suggested she come see my apartment on her way home.
In my defense, in my mind, this was an invite to merely see my stylish apartment, which I’d recently re-arranged and was proud of. No hanky-panky expected. I mean, I’m fifty-eight, not twenty-eight. I’m way past the “sex for the sake of it” part of life. I just wanted to get comfortable and show off my place.
But Maria had no way of knowing this, of course. She thought and I was out for one thing. (I am a mattress salesman after all.) And I was too clumsy at the moment to explain myself. I’d already blown it anyway.
In retrospect, my subconscious probably submarined this fledgling relationship with Maria. It’s not like me to be that pushy on dates, especially first ones. Our conversation felt forced the whole night, and perhaps I wanted to end it without saying so. I later texted an apology for being so forward and (probably pathetically) tried to explain, but Maria never replied. I can’t say I blame her.
Giant Sweater Feather
To be clear, Feather’s sweater was giant, not her. But she wasn’t exactly petite, either – which was fine with me. Her sweater nearly reached her knees even though she stood 5’10”. Feather’s height and profile sass are what drew me in, but her bad teeth cast me back out.
I can live with imperfect smiles (see part seven) and some discoloration in the dental area because my teeth are less than perfect. Feather’s, however . . . let’s just say none of her profile pics include a big smile for a reason, bless her heart. This is not a flaw I could ever get past. I’m just that kind of asshole.
Luckily, our meetup was at Hiigh Five Coffee’s Woodfin location, right beside the French Broad River. Coincidentally, the prison facility where I did time in 2014 is less than a mile up the river. Had I escaped and ridden a log I coulda stopped at this place to blend in. But I digress.
Feather and I found a nice spot by the water and enjoyed about an hour of caffeine-fueled conversation despite my considering the meeting DOA. This is where online dating can be rough and tumble beyond “ghosting” who we’d rather not see again.
I knew Feather was a no-go within the first three minutes but stuck around for an hour to be courteous. Or was I a dick for not blowing the whistle right away and saving her the hour? At least the hour spent was pleasant in this case. And I guess I deserve points for wrapping things up without promising date two.
In fact, I told her I wasn’t feeling a love match before we parted ways, and she agreed. This is the best result I could hope for in the near bloodsport of online dating.
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To place my recent dating life in perspective, I lived in Richmond, VA for six years before moving to Asheville at the start of 2023. During my Virginia time, I had dates with six women that I can recall and that’s not for a lack of trying. Covid took part of the blame, but online dating women in that town didn’t like my vibe at all, on Tinder, Match.com, Bumble, or Plenty of Fish. And it’s not like I included “ex-con” in my profile, either.
I suspect the main difference from Asheville is Richmond women consider “never been married” to be a red flag. Many of them may have their search filter set to weed out guys in this category. I’ll never understand why many women prefer one who has failed at marriage over a man who is wise or confident enough to remain single. I’m not afraid of commitment – I committed to waiting for the right one, often at the cost of profound loneliness and uncertainty.
Anyway, Asheville women seem to understand this, given that I’ve had at least a meet-up with twenty-three women in one year. And, apparently, women who don’t have kids find my profile appealing. And vice versa, I must say. Notably, Asheville seems to be home to at least ten times more childless women than Richmond is.
The point is if your dating results are not to your liking where you are, you may do well to move to a place more suitable. Sure it’s expensive and a huge hassle, but I’ve found it’s more than worth it.