Siriously? | Jill Howe

Technology is so great, helping me stay connected, helping me build my business, helping me… find dudes to date. A match.com date is like spinning a giant wheel of fate and then click click click wink. I start talking to a downtown consultant who loves to brew beer. His photo shows that he is athletic with kind eyes and that he has his shirt on (please men, stop with the selfies in the bathroom). His emails do not mention his dick or my boobs, so we go out.
We meet at The Gage downtown. He comes in right as a bar fight starts between two stock brokers. He steps over them… in his backpack. Now it’s not a rolling backpack, that would be a deal breaker, but it is still a backback. He is much shorter than he looked online. As I think this I also consider my own 5 foot stature. I tell myself to check the ego at the door with the bar fight.

After a beer, my Brooks Brothers-wearing date proposes we find a second location for dinner. We go to Le Colonial, my choice of course darling, quite possibly the most romantic place in the city for a date. French colonial Thai with huge palm fronds in every corner, cinematically muted lighting and waiters in crisp white. We are seated at the best table on the second floor veranda overlooking Rush street and we proceed to have a lovely date: backpack, mutual short stature and all.

He walks me to the red line, even though he takes the blue line. We hug, over the backpack. That’s it. A hug.
Ok, I mean I don’t need to go home with the guy on the first date, but no kiss? Maybe he’s just a little shy.

So we go out again, and this time his friends are there. He’s introducing me to his best friends, this has to be good. It is because when he hails me a cab to go home, he boldly states, with a twinkle in his hazel eyes,“You should probably take me home with you.” It’s a ballsy move, but one I want him to make. I just feel so comfortable with him, and he is just so my size-stinking cute. We are the perfect Brooks Brothers mini set. And once he has his shirt off I fully realize how he got that gymnastic scholarship to Penn State. We have an… athletic evening.

I make him French press coffee in the morning. Brooks Brothers likes a good brew and it’s true, I make a cup of kona coffee worth dating me over.

We go out again the next week to see a concert and lo and behold my touring drummer ex-boyfriend shows up. Yes, long hair and the large silver belt buckle I had made for him with an engraved lightning bolt because he goes by the nickname Mikey Lightning. Touring drummers, Brooks Brothers consultants, I don’t claim to have a type. Mikey Lightening sidles over. He was never one to be much interested in me after our short relationship, but now, with Brooks Brothers’ arm around my waist, Mikey Lightning experiences something new. The need to speak. He comes over and I introduce him, more so marveling at the vast difference between them, like a Match.com yin and yang. It’s a bit tense and I then worry that Brooks Brothers will think I am dirty for dating such a dirty drummer. He acts the same, seemingly as amused as I am about the whole thing.

We go home, and it’s a work night, so we kiss and say good night. It’s one of those kisses when you don’t want to say goodbye. The hottest kind, but also sweet, like I respect your need to sleep before work tomorrow and if we get into the same bed no one is getting any sleep.

When I am about to fall asleep I text “Dreaming of your kiss”. The perfect sexy text for the perfect sexy date. Technology, still so great.

In the morning I wake up and make that glorious cup of coffee, I reach for my phone to re-read the text and affirm my perfect dating life.

“Dreaming of your KIDS.”

Wait, what?! Oh my god, autocorrect has turned me from sexy to stalker in one single text!

“KISS! KISS!” I wrote.

Oh jesus this was getting worse. Like I said “Kiss, kiss, lover” after that.

Siri, that too smart for her own good bitch. She wants me to stay single forever, just like her! I call him and confirm that I did not want to dream about his kids, I mean, I am sure his kids would be great, our kids, no yours, but no I did not need to have them, or I could one day. Who knows? I am not opposed to kids. I mean, not now, but our kids would be so cute, they’d be so little, wouldn’t they?!

Oh my god. I could hear Siri laughing in the recesses of my phone.

A few agonizing hours later I hear from him. He was out playing soccer with his fellow consultants. Of course he was.

He handles the whole thing with as much calmness as the drummer meeting, which is to say Brooks Brothers is unflappable.

He texts,

“Are you free on Friday? We’ll get the kids a sitter”,

This man deserved another cup of coffee, old fashioned style from the French press, because sometimes technology is as great as it seems.


Jill HoweJill co-produces Story Sessions, a monthly live lit event featuring true stories connected through a theme, live music and real-time story-inspired artwork at the beautiful City Winery in the West Loop. In addition to performing her own stories at great shows like Story Club, Jill also coaches storytellers and organizes writing groups throughout the city. Find out more about Story Sessions at storysessionschicago.com.

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