Bad News with Chocolate Cake is Still Bad News

A year ago, after breaking up with a boyfriend, I found myself staring into a plate of chocolate cake, surrounded by middle-aged women giving me dating advice.

The gooey richness before me did nothing to alleviate the small death I experienced as the women — about 10 of them, some never married, most divorced (some more than once) — told me all the things I needed to do to land a guy.

These women — a group of family friends — were all dating experts, apparently. Between discussion of the best dry cleaning bargains and an unnecessarily detailed conversation about their medical problems, the women took turns sharing perspectives on the opposite sex.

Despite the generational gap (“hook-ups” and “hanging out” weren't part of their vocabulary), I found their prodding surprisingly adorable and uplifting: these women wanted to help me! But my hopeful attitude was blown to smithereens when one of them — a woman in her 60s who had briefly been married then divorced — tapped into my biggest fear.

“Sometimes it just doesn’t happen,” she said. “There’s no promise you’ll ever meet the right person so you should prepare for that.”

The other women looked at her horrified, as if my mid-20s, romantic soul wasn’t ready for such an ugly thought. And it wasn’t. She must be bitter, I thought at the time. I was annoyed. Didn’t she know she was scaring the crap out of me?

On the ride home, listening to Tom Petty and noticing how pretty Chicago can be in winter, I realized I wasn’t annoyed any more. I admired her for telling the truth — at least as she saw it.

I’ve been taught that if I go about life my way, follow my dreams, go on adventures and focus on what makes me happy, well, then it all works out. I find him. He finds me. We’re happy. Together.

But what if it’s not that easy? If we’re not going to bump into each other in some awkward but incredibly adorable first encounter at or a , should I be putting a little more effort into finding him?

It’s not like the idea of ending up alone never occurred to me. It crept in from time to time. Usually it was tucked safely in the recesses of my mind, bundled up tightly, in some distant reality where I exist in a dark bedroom surrounded by cats. It wasn’t dinner table conversation for God’s sake!

Hearing her say I might never find the right person — out loud, so assured — made it a real possibility.

So, that’s where I am right now.         

Most of the time, I’m focused on becoming the best person I can be — for me — not for the guy I hope I’ll eventually meet, and, yes, one day marry and have babies with. Growing up, learning who I am — it all feels great.

Then those women at the holiday table come back to me.

What if while I’m running around in a field of daises, learning and growing and becoming a whole, well-rounded person, my future guy is hanging out with women who read, “how to land a guy” books? What if the box I’ve naively checked in the “how to approach dating” test booklet is actually the road to Cat-Lady City?

The truth is, I’m scared. The idea of going on dates the rest of my life and never meeting the person I want to hitch my cart to is petrifying. Can I say that out loud?

Well, I am. Anyone who knows me will tell you that I can’t keep my mouth shut, especially when I’m passionate about something. Which brings me to this column.

My quest right now — and I think a journey for many women — is finding balance. On one side of the scale, I want to live my life as a complete, content human being without putting my life on hold waiting for “the one.” On the other side, I want to make sure I’m putting the right stuff out into the world so I don’t end up without a partner when the music stops, five, 10, 15 years down the line.

Every two weeks I’ll write about my hopefully exciting, sometimes crazy and always brutally honest dating tales and traumas. You’ll be along for the ride as I stumble through first dates (please, no more men who live in their parents' basements) and you’ll witness the misadventures that await in online dating sites and speed-dating socials.

I can’t promise I have any more wisdom than the next single lady, but I’ll always shoot straight. And hey, maybe an audience will help my chances of finding Mr. Right — assuming he’s really out there.

Have a column idea or want to share your own dating debacles? Tell us in the comments or connect on Facebook!