That Time I Was Named One of Chicago’s Most Eligible Singles

Chicago's Most Eligible Singles

Those of you who follow me on Facebook or Twitter likely saw back in February that I was featured in the Chicago Reader’s Valentines’ Day edition as one of Chicago’s most eligible singles. I’ve gotten quite a few questions about what happened afterwards, so I thought I’d share here how it all went down.

After jokingly posting a link on Facebook for a call for nominations, my friends Brandon and Megan went ahead and nominated me. They apparently said some wonderful things because I was notified in early February that I had been selected. A photo shoot and questionnaire would soon follow and I was encouraged to attend the Reader’s annual Valentine’s Day party at Thalia Hall in Pilsen. I was initially excited and flattered, but a bit nervous. I mean, sure I’m used to putting myself out there through this blog and elsewhere online, but putting myself out there as a 38-year-old single woman looking for love suddenly felt a bit more daunting.

I scheduled the photo shoot and my nervousness grew. The photographer asked for sizes and told me a stylist would be providing the clothing for the shoot, but I needed to do my own hair and makeup. I had hoped it would be the other way around. And then the morning of the shoot arrived – the morning of the now-infamous Super Bowl blizzard. I trudged my way through blowing snow and knee-high drifts all the way to a warehouse on the west side. By the time I got there, I definitely didn’t feel like I was looking my best and the stylist certainly didn’t help things.

The color palette for the shoot was pastels and the concept was for us to be holding giant candy hearts with different words on them. I balked at the first few they suggested for me and finally settled on one that said “Okay.” For my outfit, I rejected just about every option the stylist had in my size. A billowing button down top didn’t feel feminine enough. A cute blue dress wasn’t flattering at all once I got it on. A high-necked ruffled top was about as un-sexy as a top could be. Finally, we went with a pale green merino wool sweater and jeans – still not my ideal choice as I generally never wear pastels, but better than anything else.

It took me a while to get totally comfortable in the shoot, but in the end, there were at least a few shots that I felt pretty good about.

Chicago Reader picture 1

Chicago Reader picture 2

I was in California for work when the issue of the Reader actually hit the stands February 12.The print version was shorter than the online version, which included my answers to every single one of the 20+ questions they posed on a super detailed questionnaire. All in all, I can’t complain about how it turned out – it was me, through and through. If a guy saw it and felt inspired to reach out to me, awesome. If not, oh well. At the same time, I made the mistake of checking out the comments on the online version, which were mostly negative – people saying that none of us were worth dating (pro tip: never pay attention to online comments!!)

A few days later, I flew back from Los Angeles to attend the Reader’s Valentine’s party, dragging several friends with me. Unfortunately, while I had fun hanging out with the girls, there were no interesting guys to be found. There were a lot of couples (weird for a Valentine’s Day party) and many groups of single women, but very few men. And while the organizers had all of the eligible singles’ pictures up near the entrance with jars where interested suitors could leave notes, no one bothered to do so (with one exception – the gay man seemed to get a lot of notes).

I did get a few emails from the whole experience, but more from faculty at the law school where I work telling me they saw the feature (they were way too excited) than from any potential dates. The only email I even responded to was from a guy who looked great on paper – he had taught English in Moscow and loved to travel – but when we met in person, we just didn’t hit it off. I certainly had no expectations of suddenly meeting my perfect guy as a result of the feature, but I have to admit it was a bit disappointing that there wasn’t more interest. At the same time, I don’t know that my ideal guy (an adventurous, active guy who’s passionate about sports and travel) necessarily reads the Reader (I’ll admit I don’t).

At the end of the day, the whole experience just reaffirmed for me that I really don’t mind being single. Sure, there are a few moments throughout the year when I wish I had that special someone at my side, but for the most part, I’m pretty happy where I’m at. When I look back at guys I have dated or wanted to date in the past, I don’t think I would ever have evolved into the person I am today if I had ended up with any of them. More than anything, I never want to date (or heaven forbid, marry) a guy just for the sake of not being alone and I never want to feel like I need to be with a guy, as opposed to wanting to be with him.

So for now, the search for Mr. Right continues…

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4 thoughts on “That Time I Was Named One of Chicago’s Most Eligible Singles”

  1. Clothing can be such a reflection of your personality, I can imagine being put off by clothes someone else was trying to get me to wear that I’d never wear in real life. It sounds like an interesting experience but it sucks that not much came from it. Would’ve been nice to at least have a few dates from it. But like you said, you’re in a good place in your life and there’s no sense in being with a guy just for the sake of not being single.

  2. Good for you, Katie. I think any woman in your place would have been nervous! And I’m surprised they didn’t do your hair and make-up. I wouldn’t have been comfortable letting them choose my clothes, either.

    1. Thanks Priya! And yeah, really surprised they didn’t have someone do hair and makeup – and I would’ve felt so much more comfortable in my own clothes! They ended up asking me last minute to bring a bunch of stuff, but they didn’t tell me about the whole pastel thing so they nixed everything I brought (lots of royal blues and purples).

  3. Hi Katie,
    I arrived on your blog while searching for travel blog groups and landed on your post from 2014 where you wrote about getting off those groups :-)..
    And then I got intrigued and went through some more of your writing. It’s great! I like your style and the honesty in the posts (kind of not expected from a lawyer 😉 – just kidding).
    Looking forward to reading more..

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