Bad News with Chocolate Cake is Still Bad News

Love advice doesn't always go down easy.

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!

Betsy Brint November 21, 2011 at 01:26 PM
Hey Joanna, I am excited to follow your dating adventures here on the Patch. I've been married for 21 years - and the idea of "putting myself out there" is enough to scare me into staying married. OK, it's really the thought of getting naked in front of anyone else that keeps our vows in tact - but hey, it works for us. I know you've gotten lots of advice from your gaggle of gals - but one extra piece never hurt, right? So here it is. When chocolate cake doesn't help, move on to fries. (Commentor's thought... maybe this is why I don't want to get naked in front of anyone...) Good luck and be careful out there!
Robert K. Elder November 21, 2011 at 02:01 PM
Joanna -- Have you tried looking at the Applebee's in Northbrook? Looking forward to future columns.
Joanna Schneider November 21, 2011 at 02:35 PM
Hi Betsy, Thanks for getting the ball rolling here with a first comment! Your note made me laugh (much needed on a Monday morning!) and I'm thrilled to hear I already have one loyal reader. Regardless of how you've done it, 21 years is an impressive run--and like you said, it works for you. As for advice, bring it on! Through this column, I'll be living my dating life as an open book and I'm excited for readers to share their perspective and insights.
Pam DeFiglio (Editor) November 21, 2011 at 04:02 PM
Joanna, kudos for your honesty and forthrightness in writing this column! Consider going to Toys R Us on Black Friday, or a holiday concert at any school, and you'll see married couples and families in droves--which makes me believe it does "happen" for most people, at least when you're open to it. I'll be eager to follow what you write.
Jennifer Fisher (Editor) November 21, 2011 at 04:23 PM
I second that, Pam. I can't wait to read your upcoming columns!
Joanna Schneider November 21, 2011 at 04:30 PM
Thanks for commenting, Pam! So here's what I'm wondering: what percentage of those couples at Toys R Us are happy to be there with one another? I'm a hopeless romantic at heart but just being out and about this weekend running errands, I saw quite a few pairs that made me think "yikes!"
George Castle November 21, 2011 at 08:57 PM
I think the mere fact you're writing this column will get some inquiries for you, Joanna. The power of the bully pulpit. Other than meeting someone through third parties -- the old fix-up -- it's a total grab-bag out there, even with compatible dating sites. I think you can bring your true personality out here, and someone's going to notice it. All the while, you can give some common-sense advice to others in the same boat. Good luck!
Wayne Brasler November 21, 2011 at 09:39 PM
Barbra Streisand believes, as do I and many people I know, that the right one comes along after you have totally, and I mean totally, given up on finding the right one and figure you'll be alone forever. I was frantic from age of 12 on to find a partner; even as a 12 year old I felt like a totally unloved person with an inability to make friends. Ten years later, at 22 I was just as unloved and friendless. I gave up, totally gave up. And then, voila, as I was about to turn 25 out of the blue it happened. We met at a party and somehow I knew it was going to happen there and I had to get to that party. We were together for 30 years until death did us part. I never felt unloved and friendless again and never will.
Lisa Cisneros November 21, 2011 at 09:39 PM
Nice job Joanna! The first time my heart was broken I recall sitting in a mall food court, crying into two Cinnabons! I look forward to reading more...
Sally Higginson November 21, 2011 at 09:43 PM
Well, dear Joanna, I wholeheartedly applaud your first column and your gumption to write about living post-college, pre-death on-line. Assuming there is romance in between, it should resonate with, um, everyone. Based on your lovely photo and your age, I suspect every available guy over the age of forty will be interested. My recommendation is seek either true love, or a very very very old and very very very rich guy.
Sally Higginson November 21, 2011 at 09:46 PM
Wait. I'm not done. Make sure you don't fall prey to the worst of all situations: an attractive, divorced-with-kids guy begins dating you, you end up caring for his kids through your twenties, and then, when his kids are driving age and you begin wanting kids of your own, he decides he's not interested in a second litter. Boom. There goes your twenties, stuck in a carpool line for someone else. Don't say it couldn't happen. It happens.
Joanna Schneider November 21, 2011 at 10:00 PM
Sally, you seem like a lady who knows what's what. I hope you'll weigh in on future columns and let me know when your years of wisdom tell you I'm making awful mistakes! The trouble is, the guys my age aren't really knocking my socks off and it seems even the older ones leave me wondering when exactly the emotional maturity kicks in. That carpool line scenario sounds torturous, by the way. I'll keep an eye out for those sweet-talking divorcees.
Joanna Schneider November 21, 2011 at 10:29 PM
Also, love to see a few male voices sprinkled in here. Guys, I want to hear from you, too!
Lisa Cisneros November 21, 2011 at 11:11 PM
When all else fails, drink too much and don't wear your glasses. That's how I met my Prince Charming. Oh, and he had me at "I have perfect credit." True story. Seven years later, I can't believe how lucky I am and I am truly happy and in love. Funny how things work out.
Sara Fay November 22, 2011 at 01:34 AM
I love you, Lisa.
Lisa Cisneros November 22, 2011 at 04:54 AM
Love you Sara. :)
David Kreiman November 22, 2011 at 02:28 PM
That credit report is just as important as anything Joanna. Lisa is a wise woman!
Jackie Pilossoph November 22, 2011 at 07:06 PM
I love this and I can't wait to read the column on a regular basis! I feel like I don't know you that well, but we have worked together, so I can say this. I am ABSOLUTELY sure you won't end up alone! But one thing i have to say is, cut the guys who live in their parents basement some slack! it's this darn economy!!
Bridgette Outten November 25, 2011 at 08:33 PM
Fingers crossed for you, Joanna! Looking forward to more columns; this should be a blast =)
Richard Schulte November 25, 2011 at 08:49 PM
I thought I was going to read something about chocolate cake and got hooked into reading the article. Hmmmm, as a guy I'm sworn to silence about the "guy code", so I'm sorry, can't help you. Those other guys that commented are also sworn to secrecy-the advice they gave is just misinformation.
Lisa Cisneros November 25, 2011 at 08:53 PM
Thanks Dave! I agree. :)
Lisa Cisneros November 25, 2011 at 08:55 PM
Try speed dating. Sounds awful, but my friend met her husband at one of those things and they are very happy. Also...a speed dating session alone will make a GREAT column.
Pam DeFiglio (Editor) November 26, 2011 at 09:14 AM
So it's true about the secret 'guy code' ;-) I thought it was one of those things no one witnesses but some people swear are true, like the Loch Ness Monster.
Richard Schulte November 26, 2011 at 02:46 PM
Now we have to change the password-who told you the password was "Loch Ness Monster"?
Jessica Rosenberg November 30, 2011 at 05:07 PM
Joanna, I'm looking forward to keeping up with you. I'm in the same boat - newly singe, scared of being a crazy cat lady - but one day at a time, right? Cheers! Jessica
Joanna Schneider November 30, 2011 at 08:04 PM
Jessica, thanks for reading. The good news is we're definitely not alone. I'm guessing there's a whole sea full of smart, savvy, amazing women paddling their way through too. Up next: online dating. I hope you'll tune in on Monday!
Sarah Millard December 02, 2011 at 10:41 PM
I love this! I thought about doing a column like this myself, but my single life is not that exciting - best wishes! Enjoy the dating world!
Joanna Schneider December 02, 2011 at 10:47 PM
Love that you love it, Sarah! I'm finishing up my newest column for Monday right now, actually. Online dating can be quite the doozie.
Sarah Millard December 02, 2011 at 10:50 PM
Online dating can be a rough one....I just canceled my Match.com subscription. Really, I wasn't interested :)
Joanna Schneider December 02, 2011 at 10:55 PM
Tell me about it! I hope you'll sound off when the column goes live on Monday--looking for readers to weigh in on their own online dating dramas, disasters and happily ever afters.


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