Jump, What’s the Worst That Can Happen?

I read this piece a few weeks back at the fantastic show Serving the Sentence at Tow Bar in Roger’s Park. Check it out every second Sunday at 7 pm.

Jump, what’s the worst thing that can happen? After six years of being single, this is what I tell myself after confessing to an old coworker my copious crushing for him.

Even his name is perfect. Jack Summers**. He sounds like a made up character on Dawson’s Creek. And he has this smile. I can’t even pretend it doesn’t make me want to fall out of my shit. He owns his own condo. Getting his MBA. Has a good job. Works a 2nd one at Jcrew for the discount. He looks like he belongs in that damned catalogue with the skinny models and the Labrador retrievers, tall, dark, handsome and stylish in that way that looks like he isn’t trying too hard.

Damn. I haven’t seen or talked to him in months. It’s a week after my break up with the latest, right before the new year. I am unemployed, depressed, and have spent the last few days on an ambien high sleeping in my flannel scottie dog sheets, eating leftover Christmas fudge, and not showering. I’ve spent my time watching re-runs of The Wire, again, and eating random combinations of whatever I have in my sparse fridge or ordering large pizzas which I consume within a day. Shockingly, since unemployment and this break up, I’ve gained 15 lbs.

And bam! An email from Jack. Out of the goddamned blue. He gives me his number. Tells me to get back to him. SAY WHAT?! I lose my cool and text him back answering his question immediately.

We catch up a bit, and what the hell right?, I jump and confess my long time crush on him. Has god sent me him right now (nevermind I don’t usually believe in god)? Just a week after I dumped the last loser? The timing is honestly heavenly. We send each other photos, since I went redhead now, and because I just wanted to see his face. OMG. I forgot how cute he is. AND HE JUST SENT ME HIS PICTURE.

A few days later I’m still mourning and dealing with the loss of the last ex, and have let Jack’s face disappear from my daydreams. I’m on the delayed train back to Chicago about 5 inches into a 10 inch snowstorm, when my text message sound goes off. “What r u up to?”

OMG my heart flutters like I’m 13 and the boy at school is sort of paying attention to me. Dude is seriously hotter than Idris Elba.

I try to make conversation. I’m clearly the wittier of the two of us, which will work great as I continue to pursue my writing career and he does whatever dudes with MBAs do.

OMG my double chin! OMG my lack of employment! I totally had both of these issues under control when I last saw him. I was at the pinnacle of having my shit together, well, not really, but at the surface I was. Plus we were working at Jcrew together where the dress code made me wear so many accessories and cute shoes and all that shit so he probably gets an idea I like actually care about my appearance, when for the last 3 months I have solely worn leggings as pants.

“If it wasn’t horrible weather, I’d tell you to come into the city,” I say, all slyly.

“Ditto,” he answers. His text messages aren’t long. But all that meaning simply the word, “ditto”, I think to myself.

“Snow check?” I ask. Man I AM SO witty.

“Ha,” he replies. OMG He thinks I am FUNNY. I AM SO FUNNY, GUYS.

“Fo sho,” he says.

Ok, Jack Summers, can you tell me when that ‘fo sho’ is gonna be? Because I’m going to need to dye my roots and buy some fresh Spanx for that day.

OMG our biracial children are so going to be fucking Jcrew models. I can feel it. I’m imaging our photo shoots with Jenna Lyons and our beautiful offspring, and he asks for my email address.

OMG WHAT WILL HE SEND ME!? Oh my god. He is so thoughtful. Sent me an article on job interviewing, as he knows I have one this week. I AM IN LOVE.

Mr. Summers, YOU WILL BE MY FUTURE HUSBAND. Let’s do this.

If you are my husband, I will stop eating Express Grill cheeseburgers at 3 am. I’ll shave my legs regularly. I’ll work out. I’ll finally read War and Peace. I’ll wash all the dishes in my sink. I’ll start sleeping 8 hours a night.

Who am I kidding? I promise, I’ll try.

A few weeks later we go on our first date. He lives in the suburbs, which you know he’s cute if I’m willing to date a dude in the ‘burbs. We meet halfway at a Glenview bar to have a few drinks. I beat him there and sit at the bar, attempting to play it cool. He walks in a few minutes later, wearing a camel overcoat and plaid scarf over a Ludlow suit and Ray Bans black rimmed glasses. We hug hello. I about die.

So here I am jumping. What is the worst that can happen?

Hmm, let me see. Humiliation, heartbreak, crying rivers after he breaks my heart.

Here’s a few examples of the worst things that happened:

“I’m a Christian,” he says, emphasized at least 3 times.

“I am divorced. Just a year ago.”

“We didn’t have sex until we got married.”

“I don’t have any interest in moving back to the city.”

The man I’m infatuated with is a celibate, suburban Christian divorcee.

This may be the worst that can happen.

But what is the best?

That question and possibility is what keeps me going. Maybe this man will or won’t be the love of my life, maybe I’ll convince him to move to the city, maybe I can put off sex for a few months.

I have to keep jumping, right? Because whatever it is that’s the best possibility will always trump what is the worst.

-Melinda

**not his name

Where You Been, Girl?

Hey Melinda, where you been?

Good question. I know you’ve all missed me.

Well the short answer is I started a new job, work a 2nd and third job, been hella sick for like a month, and I’m in love.

Yep, you read correctly. I’m in love. In a relationship, like Facebook official and all that shit. Yep, it’s a true story. So writing about my dating life hasn’t been all that exciting.

But damn it’s fucking hard. We got back together. So I’m learning what’s it’s like to not be solo anymore, again.

Melinda, will you still write for this blog since you got that boyfriend?

Probably. I’ve never written this blog solely for other people. If other people read it, that’s pretty great. I still got things to say. Also, I’m going to be writing for the blog on The Tequila Tales, which is an amazing live show about love and lust, and now a blog too. I’m going to cover my transition to being in a relationship and how that all works. Because, like I said, it’s fucking hard. So Solo in the 2nd City still will be here.

And because this is my blog, I’m giving myself a shameless plug—

I’m coming back from my storytelling hibernation and reading a story tonight at Comedy Sandwich (I’m the sandwich, though my story is funny, I promise) and on Tuesday at The Seven Deadly Sins at Cafe Mustache. Come out!

<3

Melinda

Welcome Sam!

Welcome Sam!

Super excited to announce a new contributor here at SITSC. Read here for more about her adventures in single life and dating in the Second City. Welcome Sam!

Sam Bailey is an actor and writer, born and raised in Logan Square. Since she’s officially given up on getting that Columbia College acting degree, she’s been performing her own work lately at events including Salonathon, BYOB Story Hour and The Paper Machete. Sam really enjoys crappy horror movies, bougie beer, the entire Real World/Road Rules Challenge Series, and acting like she doesn’t give a fuck. Which isn’t true. She actually has all the fucks in the world to give.

Happy Valentine’s Day

Happy Valentine’s Day!

Thank you! I want to thank everyone and anyone who came out last night to our final live lit show! We love you and can’t thank you enough for your support. I’d also like to thank Beauty Bar, DJ Continental, and all of our readers. Thanks to JW Reese for designing our poster (and for reading too).

New website! As you can see we have sort of a new look to hopefully be more readable. If anyone needs like an extra project for their portfolio and wants to make a website pretty for us, I’ll send you all the love, and maybe a few bucks. Email [email protected]

All my love to Carly and welcome to a new contributor! As you may have seen, Carly, my co-founder here at Solo in the 2nd City will be moving on to greater things. Since I know you don’t want to only hear about my sad dating life, I am welcoming a new contributor to the blog. Woot! I’m going to officially welcome and introduce her on Monday, so look out.

In the meantime, please enjoy your weekend. Don’t be a hater to Valentine’s Day and instead enjoy all the love you have for your friends, family, chocolate, and wine.