hopeful. Sometimes I would even buy something just to buy something. It wasn’t exactly what I was looking for, but it was there, so I grabbed it while I could.
Like discount shopping, dating in my forties meant grabbing the most passable thing I could find because one can’t leave empty-handed, but by the time I got home, exhausted from scouring the discount racks for something I didn’t even really love, pretending it would work, I was always left with nothing but regrets. Sure, I’d use it once or twice, hoping it would eventually fit, or look better than I expected. But each time, I learned it was never going to change. Frequently, it just came up short and I eventually discarded or donated it, disappointed yet again.
When I was in my twenties, trying to find a partner felt easier, not that I landed one. Dating in your twenties is more like going through the racks at Bergdorf or Saks. The available inventory is generally high-quality, and there’s so much more of it—lots of styles, sizes, and colors. You can take your time and look through the racks, try on ridiculous things for fun or things that you know will be great, and consider some wackier ones that you’re not sure about. You can splurge and buy something crazy without worrying about the long-term ramifications of having spent your money on a feather-trimmed go-go bolero jacket and having none left for practical black work pants that will last you a decade.
When you are young, you might even be brave enough to buy something you can’t quite afford, but that dazzles you, then wear it once and return it with the tags still intact. And if you’re broke, you can still window-shop and never actually commit to a single item. There’s joy in that.
I dated like that when I was young, but what I didn’t realize was that I wouldn’t always have the luxury of making foolish or frivolous purchases. Time runs out on that eventually.
When you’re in your thirties, you are more likely searching (somewhat frantically) for the father of your child, and maybe feeling somewhat desperate about it. The pressure is really on. The clock is ticking. The inventory is shrinking. Judgment is clouded.
For me, dating in my thirties looked like that episode of Laverne & Shirley when they won a shopping spree at a grocery store. They were on the clock, and whatever groceries they could get across the line before time ran out, they got to keep. (As a kid I watched this episode with my dad, and he told me if I ever won a shopping spree just to grab all the steak because it’s the most expensive item in the store. #LifeLesson #HoldingOutHopeToWinAShoppingSpree.)
Laverne and Shirley overloaded their cart, stuffed items down their pants, and ultimately couldn’t carry everything they had hopelessly grabbed, let alone walk to the finish line, so by the time they dragged themselves to the end, the only items they got to keep were fish sticks and scooter pies. Junk. Limited value added.
They wanted too much, shot too high. They had big expectations and, in the end, got next to nothing.
Restocking the Dating Shelf
A couple of years into my new career as a ghostwriter, I started to get my professional stride. In the career category, early signs indicated that the Universe had been onto something.
There was a steady-ish stream of work coming in, and while I never exactly became a calm and relaxed person in terms of worrying about paying the bills, I had enough work coming in to keep me going. That meant I spent 100 percent of my time focusing on building that business. Losing a job, freaking out about it non-stop, and making radical career choices based on the Universe allowed for little else. That was all the capacity I had at the time.
I was no longer the multi-tasking producer I once had been. Sectioning my life into separate entities was suddenly how I began to get by. That meant, since business was going okay and I was gaining momentum working for myself, it was probably time to start to pay attention to some other aspects of my life.
Dating seemed the obvious aspect to tackle first. That’s what all the books said, anyway.
One book I was working on chronicled the dating disasters of a celebrity and all her friends. I was interviewing a long list of women about their dating calamities. One of my favorite stories involved a woman crawling out the bathroom window at a restaurant to escape a horrible first date. These women, all of them, went on tons and tons of dates—they were playing the volume game. By sheer odds alone, it felt like each one of them would eventually meet someone because they were putting effort into it. I found myself cheering them on as I wrote their stories, thinking each time they were getting closer to finding a match.
That inspired me. And since I had made it a habit to put into practice whatever book I was writing, I at least had to try to get back out there.
Like any decent self-help convert, I assessed both the holes in my own life and the available and appropriate experts to help me fix them.
Shopping analogies aside, my first consideration as I developed a strategy was taking an honest account of my dating life. I could sum it up simply by saying: Nobody had really been all that interested. Not for the long haul anyway.
Period.
But that would make for a boring and short chapter and would also not leave much room for self-reflection.
Also, I was working from home, so not only did I not have access to people “at work,” I had substantially less interaction with humans in general. (Ask anybody who works from home: It’s a lot of alone time.) I needed inventory.
And I had to widen my pool—laws of attraction and all that aside, this was also a numbers game. And in fairness, statistically, the numbers weren’t exactly on my side. One stat I found said that there were, apparently, eighty-six single men for every hundred single women. Another—thirty-three available men for every fifty women.
Those numbers rang particularly true in New York. Cities like Portland and Seattle, from what I read, seemed to have better odds, but before I moved across the country seeking Mr. Right, I was certain I could find simpler ways to beat them.
Factoring in age, those numbers were probably worse. The inventory was obviously better when I was younger. But my methodology for finding a single man, any single man, was going to be harder. I went on blinders (my word for a blind date) back in the day. Back in my twenties, my friends had people to set me up with. And there were some good dates that maybe I should have given more consideration. At the time, though, I was often sent away on an assignment and I ended up brushing off many of those good ones.
Ultimately, my friends ran out of options, or more likely hope—I am not sure which one. Either way, I could no longer count on that method to boost my dating inventory and my odds.
Choosing to ease my anxiety, I swore off speed dating. It was efficient, sure. But I had endured the humiliation of it too many times to give it another chance. If you haven’t done it, picture this: The women in attendance took a seat at a restaurant—either at various separate tables, or in one instance a U-shaped bar with upholstered benches hugging the wall. We remained stationary while the guys circulated through. Depending on the set-up, I would experience between ten and thirty “dates” lasting between three and five minutes each. It was exhausting, torturous, and beauty-pageant-esque.
Kill me. Please.
To round out my plan, I had to be honest with myself about my abilities. One final consideration as I planned to embark upon my dating mission: a quick self-assessment made me start to suspect that I had limited skills, making the shopping that much more challenging. I read the hit book The Rules way back when it came out, but I’d also fully ignored all the rules they offered up. For example, if you called me on a Thursday back then (or now) for a date on a Friday, I’d break the not-past-Wednesday thing and say yes.
Read: Desperate. Why? Because I dated by employing the same tenacious techniques that I had as a journalist.
Unrelenting.
Make it happen.
Pin it down.
Hot pursuit.
Get the interview at all cost.
Call until the source says yes.
In