I moved to Chicago after I graduated from law school, nearly ten years ago. I had a nice little place in River North with a view of a tiny slice of the Chicago River and the Sears Tower (it was still called the Sears Tower back then—times were simpler). I got new furniture for my living room, a sensible bed that had drawers and a shelf built in, and an awesome Buddha piece from Pier One Imports for my bedroom. I was on my way.
Although I had lived in the Chicago area my entire life, save the 7 years I spent at Indiana University for undergrad and law school, living in Chicago proper was new for me. Most of my closest friends were in other states. I was, not surprisingly, anxious about my social life in the big city. So, I did what any *smart person would do. I responded to a sign that said River North Singles.
*No smart person would do this.
I called the number (hey, remember when people used their phones to call numbers?) I made an appointment to meet with someone. I walked over to the John Hancock building after work at my brand new job—my first job out of law school. I rode the elevator up, up, up….to one of the weirdest conversations I would ever have.
It was a small office composed entirely of well-dressed women. I’m going to be honest, this is not what I expected when I called the number. I didn’t expect to have a meeting to discuss my status as a “River North single.” I kind of figured there would be a website I could visit, or a group I could join to meet other people. Nope, there was an office.
This was a long time ago, so the details are fuzzy, but I do remember sitting in a small room with a woman who explained that they were, basically, a dating service. Suddenly, I felt completely trapped. Like I was accidently in the closing room at a car dealership. The woman chatted me up a bit about what I was looking for in a partner (I mentioned that I was Jewish). Then she handed me a binder full of men containing plastic coated pages of pictures and profiles, like I was a casting director. Then, she left the room and asked me to look through them.
There were a bunch of Jewish men in the binder, several of whom I had already gone out with. Was this really happening? Was Rod Serling going to pop out from behind the wall, cigarette in hand and say “in this tiny, poorly lit room, sits Tiffany gazing through a binder of potential suitors. In a minute, Tiffany is about to have a terribly offensive conversation with a pushy woman and go home feeling more dejected than ever because she has now entered the Twilight Zone.”
A few minutes after I started flipping through the book, a different, better dressed woman entered the room. She was, clearly “the closer.” She asked if I liked anything I saw. I told her—in the nicest way a people pleaser can say it— no. Then she said the following. I will always remember it. “Tiffany, you just moved to Chicago, right? So, you bought a new couch, right? Don’t you want someone to sit on that couch with?” You guys, that really hurt. A lot. And I almost took the bait. But it was also insanely hilarious at the same time. In that moment, I decided I would find someone to sit on my couch with, but I was going to do it without the help of a closer.
I did end up meeting someone and getting married and, in subsequent years, we constantly complained about how our couch was way too small for the two of us.
Am I thrilled to be out there again? Fuck no. I keep thinking about the late Carrie Fisher and my personal favorite roll she played, Marie in When Harry Met Sally. In once classic scene, she turns to her partner, Jess, as they are lying in bed and says “tell me I’ll never have to be out there again.” I said those same words to my husband, but life is not always predictable. Scratch that, it’s never predictable.
So, I’m out there and, oh boy, is it the wild west. When I was on the market, 8 years ago, I was on Jdate. It was pretty simple. Write a profile, connect with a guy, go on a date. Now, it’s all about the dating apps. I wonder how many calories you can burn swiping left and right. Today I got a push notification from Hinge, a dating app, that said “we like Boomer for you.” Boomer! I’ve seen too many shirtless dudes, guys holding babies and then proclaiming in their profiles “not my baby!” and everything in between.
I’ve said this before and I’ll say it again. Loss and pain are incredible teachers. If we are willing to do the work, they can teach us how to be better versions of ourselves. So, although I’m still feeling my way through these changes, I can say that I am a lot more comfortable in my skin and know what I want. It’s just a matter of finding it. I’m confident I will because it turns out I’m pretty rad.
On my 25th birthday, during my last year of law school, my dear friend sat me down and shoved a piece of paper and a pen in front of me. “I’m tired of hearing you complain. I want you to sit here and write all of the things you are looking for in a guy!” I obeyed. I’m an entirely different person now. So, I think it’s time for a new list.
I bet you’re wondering whatever became of that couch, aren’t you? The couch of doom. The couch that a well dressed woman once told me I needed to share with someone. I’m actually sitting on that couch as I write this, only I’ve pulled out the bed beneath it and thrown a memory foam mattress topper on it. It’s glorious and it’s all mine. It’s where I do my writing now, under a blanket that looks like a leopard. That’s the thing I’ve learned about being single again. Things that once felt small feel large again. Like my life.