The Dating Game

Author: Paige Smoron Wiser '92

I honestly can’t think of any advice my mom gave me about dating. She’d pretty much let me muddle my way through, with an eyebrow raised here or there. That is, until I’d bring home a guy she really couldn’t stand. Then she’d let me know about it.

I remember one year when she took a photo of me with my high school homecoming date. The spot where he was standing was obscured by a mysterious black bar of undeveloped film, as if God—or Mr. Kodak himself—didn’t approve, either.

My parents separated when I was a teenager. Nothing dramatic, nothing messy; just an unspoken legacy that I was to avoid the big mistake they had made: settling down early. Or, as Smokey Robinson’s mama more specifically told him, “You better shop around.”

It’s not as fun as it sounds, of course — but it occasionally came close. As far as men were concerned, I had the good fortune to be restricted by neither type nor taste. I fell in love (truly, madly, deeply) more times than is strictly advised. And I stayed in the game long enough to notice my priorities changing (from “You should see him put away the Jim Beam!” to “He has excellent equity, I checked it out”).

When I married at 31, I had been officially dating for half my life. I devoted a great deal of energy to it, and I seldom gave myself time off. Near the end of my career as a single, I’d gotten so efficient that I could take one look at a guy and immediately know how long the relationship would last, what nonhygienic habit of his would drive me crazy, whether we’d fight more over money or his family, if my sobbing would be of the silently streaming or hiccupping variety, and if I’d have to change my phone number at the end of it all.

Sometimes I’d date him anyway.

I do wonder what my life would have been like if I’d met my husband when I was younger. I watched my little brother marry his college sweetheart (brilliant, red-haired, born on Saint Patrick’s Day), and they made it seem so easy. They still look at each other with the unembarrassed adoration of a first crush.

The rest of us — who spent any amount of time “out there” — got a bit damaged over the years. We earned an education in entanglements. Our hearts were broken, and we had to learn to protect them.

But I will say this: We have better stories.

It’s probably a bad idea to print mine here. Rather than attempt to describe the men I’ve dated, allow me to list just a few of the reasons we broke up: another woman; his strong sense of thrift; a reverence for the Virgin Mary that took precedence over me; probably gay; a drink called the Zombie that must have contained an unusually blunt strain of truth serum; chronically misused vocabulary words (his); he simply “forgot” to pick me up for dinner one night; my impatience; my nagging; my general dislike of the Great Outdoors.

Dating at Notre Dame, of course, was absolutely no preparation for the real thing. Flirting over snickerdoodles in the dining hall, swapping blind dates at SYRs—it just didn’t translate to the single life in Chicago. Once I graduated, I was never again formally asked to Sunday night dorm Mass.

We were somewhat spoiled by the dating selection at Notre Dame. The freshman Dogbook was comparison shopping at its most convenient. And character references were easy to come by.

In the real world, you can’t quite be sure what you’re getting. And after budgeting for eye-catching hosiery, breath mints and cab fare home, there’s not much left over for private detectives. I once accepted a marriage proposal—and a respectable diamond solitaire—from a gentleman who, among other omissions, had neglected to tell me his real name.

Things didn’t work out.

It’s nearly impossible to avoid a dating disaster or two. The system is set up for failure. Think about it: We’re taught that there’s at least one guy out there that we should, in theory, be able to stand for life. We just have to find him (though he may be disguised in bad plaid). I always found the word “hunt” to be more apt than “courtship.”

I’ll admit that I never had a hard time meeting people. As a young newspaper reporter, I didn’t realize you could separate your work and social life. Desperate for a byline, I once accepted an assignment to sample five dating services for a month. It never occurred to me that everyone else in the office —rolling their eyes—had already passed on it. I asked myself, “Would my editors want me to write a story that wasn’t entirely dignified?”

Thirty days and 25 blind dates later, I had my answer. The high point was the guy who picked me up in a Ferrari to go to a Bulls game (back when they were good). The low point? The guy who invited me over to watch the Star Wars trilogy and drink sake. Although, to be honest, I rather enjoyed that, too.

The single life isn’t anything like our parents—or the movies, or Social Dance class—said it would be. It’s a numbers game, and an almost unimaginably cruel one at that. Now, even matchmaking websites are turning away candidates. If two people do manage to come together, for mutual awkward conversation and cocktails, the overwhelming odds are that at least one of them will be rejected. The all-purpose line we reserve for difficult situations—"It’s nothing personal"—just doesn’t apply. There’s nothing more personal.

I never complained that there are “no good ones out there.” The problem is that we aren’t always in the mood for a good one. For me, time took care of that.

My husband is nothing like I’d envisioned he’d be. He’s not one of the brash young Ferragamo heirs, for one thing. And yet the night he asked me out, it took me just one bottle of chardonnay to fall in love. Or maybe two, but you understand what I’m getting at. There are some perks to dating to the point of being jaded: When a keeper comes along, you know it.

He passed all my time-honored tests. Smart? Check. Funny? Check. Big blue eyes that see right through my usual tricks? Check. Suitable for road trips? Check. Picks up his share of the checks? Check. Lively first fight? Check.

Even Mom approves.

He’s got his own dating stories, of course, which we studiously avoid. But he did let me in on his predominant romantic strategy: “You throw enough [stuff] against the wall, something’s going to stick.”

I stuck.

The contented married life was the goal—and sometimes when I watch him sleeping, I wonder how I got so lucky. But obviously, there are things I miss about being single. I rarely have a legitimate reason to wear my leopard miniskirt anymore, for instance. I no longer am allowed to stay out all night (not that I would, but I could). Dating is about possibility and potential; marriage is about “making it work.”

Most of my friends are still single, and I love hearing about the glamorous weekend trips they take and the gorgeous rocket scientists who ask them out. Luckily, my envy is tempered by their scarier stories. (A girlfriend just today e-mailed me: “A guy I once went on a blind date with is now calling me several times a day from his mental institution, asking if I understand that every time President Bush says the word ‘challenge,’ he’s actually sending him a secret message, since his name is Charlie and it sounds an awful lot like challenge.”)

The hardest part of the single life is the uncertainty: How is it all going to turn out? We’d enjoy it a lot more if we were assured of a happy ending.

That said, I realize that marriage isn’t for everyone. I applaud my strong, independent friends who may keep dog paddling in the dating pool for years and years. Or maybe they’ll decide that they prefer to be on their own. I know that they shouldn’t need another person to define and validate them.

But then I think: These are great people. They deserve to share their lives with someone.

I’m due to give birth any day now to my first, and my single life seems very long ago. I’m not sure what I’ll tell my daughter when it’s her turn to date. “Respect yourself,” I’ll say, and “Keep an open mind” and “Drop that loser now.” But I know she’ll probably learn as much from the things that I don’t say.

If I can tell her one thing, I’d like it to be this: Each time your heart gets battered, it heals a little bit bigger.

And then I’ll let her muddle her way through

Paige Wiser is a columnist for the Chicago Sun-Times.