A speed dating success story <3


I knew going in…it would be interesting. Possibly wonderful. Probably disastrous.

Either way, I knew it would be exciting. Nerve-racking. Different.

I try to make sure to do new things when I can. Things that scare me. Branch out beyond my bubble.

And for a millennial, addicted to my smartphone and used to swiping occasionally on dating apps, Speed Dating was quite the branch. 

We arrived with time to spare, climbing down an entryway staircase to a dark, dimly lit lounge in Old Town. A round of drinks was needed. White wine was on my mind.

I glanced around the bar to see what type of men I’d be chatting with. With an age range of 25-40 years old, we weren’t sure what we were in store for.

There was a younger guy, clearly wasted (by 7pm on a Saturday, no less), and there with two girls. Dancing with reckless abandon. Clearly drunk. Falling over. A few minutes before we got started, I wondered how atrocious it was going to be to get through a conversation with him as one of the dates. Luckily, him and his “friends” were escorted out. They were not a part of the night’s festivities. Phew!

The women were instructed to take a seat at their designated tables, and eventually the men would rotate around to each of us. My two friends and I were seated at 3 high tops all in a row, against a wall.

It looked like a game show. Picture a modern version of The Dating Game. I half imagined a man to come out on a stage behind a wall and ask “What is Bachelorette #1’s idea of a perfect date?”

Women sitting and men moving seemed ideal – we didn’t have to do much, just wait for the next guy to take a seat. But waiting for that first guy to “start” the first round seemed to last an eternity. I’ve never felt more on the display. (And I recently did a burlesque show – ha!)

Each person was assigned a number (which would come in handy later). Then given a card to fill out with your comments/notes for yourself, and, ultimately, a Top 5 section for the names/numbers of the people you wanted to talk to in the future.

If someone else also put you in their Top 5, the event would let you know you’d been a match. If not, no harm, no foul. (just some bruised egos)

We were asked to keep the cards confidential, and potentially even turn them over when someone else was at your table (so they couldn’t see your rankings).

First guy. First conversation. My first time speed dating. I led with that.

I thought it would be easy conversation to discuss the novelty of the night. I was wrong. My first guy had done this before. Had been asked back for some reason. Had been to the same bar. And done the same thing. Not sure how I felt about that.

His shyness reminded me that I was indeed skilled in chit chat. I pried a few interesting stories out of him, and while I wasn’t into him at all, I never let a good convo go to waste.  I was in for a long night of such dialogues.

The second guy introduced himself quickly, but with his accent, and my ear close to the speaker in the bar, I didn’t quite catch it.

Ahhh. That’s how the numbers help. Now I had a way to identify him without re-asking his name – which felt a little awkward. Subsequently, I introduced myself as “Rose#3” the entire night. All one word. Ha.

The night was beyond entertaining. Like an anthropological study in heterosexual, human interactions. Being a bit out of the dating circuit for the last few months, I wasn’t certain if I’d be off my game.

Not sure what I was worried about.

There was so many hard-to-describe conversations, but I’ll try to capture a few of the funniest moments of the evening.

It’s a small world, after all
One particular gentleman was so enchanted with Disney World, he talked to me about the pros (no cons) of going as an adult for essentially the entire 7 minutes. It did not seem to faze him that the first thing I said before he began his verbose filibuster was that I, indeed, do not love Disney. He didn’t care. He needed me to know that Cinderella’s Castle was beautiful under the glow of fireworks at night – no, I’m not kidding. The real question is…does he get commission for every stranger he convinces to jet off to Orlando?

Driving for the City
The most hilarious answer of the night to the question “what do you do?” was a concise: “I drive for the City.” No further explanation. I had so many follow-up questions racing through my brain. What do you drive? Do you drive a bus? Do you chauffeur the mayor? No judgment. Just confusion. After some coaxing, he went on to explain that he was there to help with various issues in Chicago – from snow salting to water flooding, etc. And so, I inquired, “Wait, do you work for Public Works?” And he replied: “Oh…Yes!” He was so excited that I guessed it right he smiled big and bold, and even gently caressed my knee. Lucky me. WTF.

Don’t plan on it
I had the most in common with one guy, but there was an issue. He was in event planning. He did event planning. He worked for an event planning company. Did I mention that he planned events? …And so he left after 7 minutes having shared the equivalent of a TED talk about his day job…without ever bothering to ask me my own profession. Social skills – hard to find apparently. On to the next.

…At this point, you may be wondering. Was I exhausted? A little. But the second round of Sauv Blanc didn’t hurt.

There was also a break in the festivities – there was 1-2 more women than men that night. (And apparently one guy left…possibly out of nerves? Aw!!)

It was a nice chance to take a breath, and check over my “notes.” Was anyone piquing my interest? Not so much. Some were nice. But odd. Some were cute. But a bit off. I could sense that many of these men were a little starved for attention.

And, honestly, I can’t really relate. I’m just fine on my own.

I know that I’m not “supposed” to think that. I’m supposed to say I have compassion and empathy for these guys. And I do. I just ALSO feel strongly in my self confidence.

Now, the older gentlemen of the group, who clearly found some sort of loophole in the 40-year age limit, were at least the most engaging guys to talk to. They found me charming and novel. I found them grounded, yet we had very little in common. Their previous marriages and knowledge of Frasier at least produced interesting conversation (I’m binge-watching it on Netflix at the moment).

I appreciated that one of them wrote me down in his Top 5 in front of me. That’s actually a pretty solid move. #TopFiveLife

Something that surprised me was the sheer distance some of these men had traveled to be there. To come into the city from the suburbs, including NW Indiana, seemed a long way to go. Worst case scenario = a long, depressed drive home. Best case scenario = a basically long-distance relationship with a girl from the city. But I digress.

My favorite line of the night was: “I’m really into Midwestern girls.” Ick. You might as well be the guy who told me on Bumble last week that he’s a “legs man.” Blergh.

What is wrong with people?

A pattern emerged as the night went on. With many of the men telling me they’d done this before. Oh, and many telling me they’d come talk to me “afterwards.”

Was this some sort of code? Some sort of ritual in the SD community? Was there a subculture for Speed Dating? (or a subreddit? ha)

As the night eventually came to a close, not one person approached me again.

A few of them chatted up my friends, likely hoping to seal the deal on their respective rankings perhaps. And as I waited at the bar to close my tab, avoiding eye contact at all costs with the men I had just had 12 (rapid) first dates with, I realized I forgot to turn in my card with my matches. My friend offered to grab it.

I thought about adding someone to the Top 5 before turning it in to the event hostess. But I was having trouble. My gut told me to put no one. And why should I? I had fun. I paid to be there. But there’s no contract. I don’t have to talk to anyone I don’t want to ever again.

For me personally, the only reasons I would be writing anyone down is trying not to hurt someone’s feelings, out of fear of being alone, or out of fear of breaking social norms. But, I’ve been so busy lately living that #bossbabelife (cliché, I know!) that I’m trying to reserve my free time for people and things that bring me joy!

As my friend returned, she explained she had turned in my card for me. “Who did you pick?” she asked.

“No one,” I said.

But that wasn’t true. I did pick someone: Me.

Corny? YUP. Don’t care.

I found a little love at Speed Dating. But it was for myself. For my friends. For my own energy. Own story. Own amazing future.

I’m #1 in my happily ever after…I’m my own Top 5, baby.


Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Back To Top
%d bloggers like this: