I walked up to the bar. There was a cosmopolitan freshly poured.
As I went to pull out my chair, he said, “We’ve been waiting for you.”
And yes, I mean “we”.
We were on the roofop at the Godfrey Hotel, a respectable place for a first date in Chicago.
“Your friend has told me a lot about you,” he went on.
And by my friend, he means the one who is sitting next to him. Because this is her date. I’m just here for the cosmo and moral support.
We finished our drinks at the bar, and then we got a table.
I went to look at the sunset and give them some space. But, after 15 minutes, I came back, and there we were, the three of us, still doing this.
So, what is this?
Is it cool to bring a friend on a date?
In the era of swiping, texting, and speed dating via apps, some of us feel it necessary to make these “hangout session” less formal and more informal. (But seriously how can you be more informal than Netflix and chill? I mean I’m looking at my last two dates that showed up in sweatpants.)
After we finished the calamari, and the man of the hour had an allergic reaction (don’t worry, not like in Hitch), my friend took his hand and walked with him to Walgreens.
My work here as the third wheel, was done.
To say, that this was my first time in one of these dynamics would be a lie. I think it’s natural to bring a Tinder date to a party or event, but sometimes that seems like too much pressure for a first date.You don’t want to be that girl that always has a different man with you on weekdays. Am I supposed to introduce you to all of my friends when I don’t even know exactly what you look like or who you are? More importantly, how am I supposed to find you?
I did it once during St. Patrick’s Day. I invited a guy to hangout with my group of friends and have drinks at Rock Bottom. It was actually one of my favorite dating stories.
But then there was this time I invited a guy to meetup with me and my friends. And then, we went to a bar and hung out with his friends. The night continued to another bar where his best friend hung out with us all night. It got to the point where I felt like I had to find another date because it felt like the two of them were inseparable. And, on my own date I felt more like the third wheel. So, I did what any girl would do. I walked out of the bar to go home, and they ran out after me. But wait, his friend took us back to my place.
How comfortable is too comfortable on a date?
I think it’s important to be comfortable on a date. You shouldn’t wear that tight dress you can’t breathe in.
But sweatpants? No.
Asking for dinner on a Netflix and Chill date? No.
Bringing a third wheel? I’m going to say no.
It’s nice to get a free cosmo on a date and have no obligation to talk to the guy again because he’s not your date, but it’s weird. It is.
Not to mention, what if you both like the guy.
I talked with a few friends at a cocktail party about it and they do the same thing. My friend brings her gay best friend with her on dates. He gets free drinks and she feels more comfortable.
There’s always a tug of war between the best friend the guy you are seeing. I tend to keep the men I’m dating private because we never reached a point for us to actually be an item.
But what are your thoughts? Are you team three is company or three is a crowd?
Amanda Elliott is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.