Lady Jane – Resident Taken Lady. Romantic Realist. Real nerd.

For sentimental reasons.

Welcome to the first post of the resident “taken” relationship lady – Lady Jane. I know, I can hear you booing, hissing, and puking from here.

I was a #singlelady not too long ago, but somehow, somewhere in the timeline of my life, I became a serial monogamist, despite my proclamations of “not wanting a relationship” and “just wanting to be single.” I treated guys like boomerangs – I’d throw them away immediately, but if I threw them correctly (or sometimes really incorrectly), they’d come flying back and I’d be so surprised and impressed that the boomerang actually worked like it should that I’d hold onto it with curious admiration and love until ultimately I’d run out of ways to throw that boomerang and I’d leave it in the park for someone else to play with. I suck at metaphors.

I moved back to Chicago about a year ago, after a brief stint in LA, and took a “relationship break.” I didn’t casually date much in college and I felt like it was my time to shine! And I did. I dated and had what I’d consider a healthy amount of casual encounters. I felt wanted and it made me happy (remember – stay safe!). I got to explore and build upon my sexual interests, something that had been stunted in my previous relationship(s). More on that later.

For future reference: I tend to get technical about my sexuality and romantic experiences. It’s my “sexy talk.”

This was the best "sexy science" gif I could find.

Six months into my “break” – BAM. I meet Jack*. Six months later, on the one year anniversary of my return, flash to me here writing a bragging blog post about how happy I am and how great he is and blah blah blah – because the masses love that shit, obviously. Joking aside – I am quite - well, ridiculously happy in my relationship. So far we just… work. It’s gross. I’m channeling my inner hippy and going with the flow. Double gross.

What are my goals in this blog? To share my little nuggets about dating and relationships and to assist my lady friends with Operation #wtcba. Think of me as the resident old lady who starts her blog posts with “back in my day…” or gives you an unwarranted and unwanted sex tip because she’s old and wants to enrich your life while making herself feel young again. I’m secretly 75.

That might be canon.

Goodbye for now,

Lady Jane

*Name changed because, you know, internet stuff.

WTCBA: Week in Review

Boys Boys Boys

This was a particularly successful week for Where the Cute Boys At. Let’s review:

Where were the cute boys at this week?

Holiday Club (4000 N Sheridan Rd)

Holiday Club was graced with more than one of us, more than once this week. We started off the week at Geeks Who Drink on Tuesday night. The plan was to impress all the cute boys with our knowledge, but instead we ended up with this:

"Super Smash Bros" is the new "IDK"

 A shoutout to Quiz Master Andy for asking all the cute boys to raise their hands for us. We appreciate your commitment to the cause, and you can be sure we’ll be back again.

But wait, there’s more! We returned Thursday evening for Rat Pack Comedy/Blackhawks Playoffs game. There were some cuties present at comedy night, and we even talked to one. That’s right. My confidence-lacking, introverted self went up to a cute boy and said, “hi.” After that the anxiety took over and I might have asked if he likes pickles. Strangely enough, he politely excused himself a minute later and then avoided eye contact when he left the bar. Oh well. Any man of mine needs to share my pickle enthusiasm anyway. 

At this point, suffering just enough rejection and witnessing a miserable Hawks game, it was a good time to close out tabs and head out the door. But as we switched from the back bar to the front, we were confronted with a sea* of boys. (There were three. Maybe four). We stayed, and it was well worth it. We made a new friend, we did blueberry bombs, we danced, we gave out our numbers, and we kissed some boy. Just one. SUCCESS.

The Red Line:

Shout out to all of the cute boys reading on the red line this week. Keep it literary.

Map Room:

This night went off the rails. We had a plan. We had stops to make. We had boys to find. But Map Room came with seemingly hundreds of National Geographics, some good tunes, and…. bartenders that gave us a lot of free shots. We’ll hit up the rest of Bucktown soon, but Map Room + cute bartenders + free shots is an equation for success. Special thanks to the Tamale Guy. I would not have survived the last shot of the night without you. 

A hero among men

Two observations from Friday night’s debauchery:

1. If I do a shot of Malort, it means that I am already drunk and am trying to impress you, and if I’m trying to impress you, that means I think you are cute. Cute boys of Chicago: please file that for later. If any girl voluntarily drinks a shot of that vile mosquito repellent, you better A.) Get her a glass of water and B.) marvel her beauty, grace, and charm.
2. Flirting with the bartender is an intricate game. I’m not new to this one, but generally, the cute bartender just wants to you tip well and maybe check out your butt. Keep a weather eye for cues otherwise, but you must usually prepare yourself for that awkward “it’s closing time, please leave and do not wait for me” conversation. Sometimes, however, that conversation doesn’t happen. Sometimes you may stay at the bar after close. Relish those nights. Raise a glass to your youth and take a bow. 
   
   
   
   
   That's all for now, folks. 
   
   
   Have suggestions for where to meet the cute boys? Leave your tips in the comments.

You Make a Grown Man Cry

This week, on WTCBA, we bring you the story of Dave* and invite you to listen to this Rolling Stones classic: 

Origin: OkCupid

Age: 31

Occupation: Animal care
Match Percent: 74

The story of Dave begins like a majority of OkCupid dates. A few back and forths about jobs, movies, weekends, how great alcohol is, etc. before moving onto the exchange of phone numbers and suggestion of a date.

What really distinguishes Dave from your average OkCupid date, however, was the moderately high chance that I may or may not have seen this guy on the train in February.

And possibly took a picture.

This picture.

A cute boy in the wild

He was cute. What can I say.

Anyway. It took a few runs through Dave's profile before I realized that he looked very, very similar to the man pictured above. Leading up to the date, I was placing it at a 90% chance that Serendipity had matched me with the hottie from the Red line.

Dave walked through the doors of Hopleaf and it was regretfully not the guy I had hardcore creeped on (although, he was still pretty cute). I was expecting a fantastic story to tell our grandchildren (“Nana creeped a picture of your Grandpa on the red line and got QuickMatched with him weeks later. #fate #truelove.”) Alas.

Onto some date analysis:

Conversation: Dave had memorized my profile. And not just my favorite movie or the "most private thing" about myself. No. Homie had memorized how I answered my match questions. He quoted my profile. I would say he was a Grade A Creeper, but this is coming from someone that took a picture of a cute guy on the red line, so I’m probably not allowed to judge much.

Notable quotes: "I've been smelling you all night." Was I wearing perfume? Sure. Did that make this statement less weird? HELL NO.

Financial analysis: Dave was late, so I paid for my first beer while I waited for him to show up. Once he got there and it was time for a second round, he made no motion or effort to pay for my drink. When it came to his own, he ordered the cheapest beer and tipped an aggregate sum of $1 for the four beers that he had.

Actual physical appearance v OkCupid: No smoke and mirrors on this guy. He looked like his profile, so there was no knee-jerk reaction. The 2-inch rule did apply, however. Ladies: always mentally subtract two inches from their given height. Always. And if the height is blank on their profile RUN AWAY. This means they are under 5 feet tall.

Despite having some strikes against him, Dave was overall a very nice, polite young man. He was easy enough to talk to and pretty easy on the eyes. When he offered to walk me home, I counter-offered with an invitation to play some MarioKart. (Because I know what boys like).

MarioKart never happened. As soon as we got to my place, Dave went straight to Make Out City and he was the mayor. I rolled with it, because kissing boys is one of my favorite hobbies and ranks just a hair higher than MarioKart (but not by much).

And then… perhaps 90 seconds later… it happened.

Homie burst into tears.

And I’m not talking one rogue tear. He was heaving. Sobbing. Ugly crying. There was snot.  

Why the waterworks, you ask? Blame the majesty of my right boob. His grabby little hands made impact with ole' righty, and the glory of the boob overcame him instantly. (Apparently the gentleman had never actually touched a boob he wasn't in a long-term relationship with before and he was very overwhelmed).

Needless to say, I very kindly and gently suggested that maybe it would be best if he went home and cried, which prompted a dramatic "SO YOU JUST NEVER WANT TO SEE ME AGAIN?"

Um. That is correct, sir. Now please leave. 






*Name redacted to protect Dave's fragile, fragile emotional state.

Let's try something different

So, after that stirring first post by our fearless leader, Madame X (her name is currently lost to the universe), I thought I'd share my fascinating and compelling back-story.

After years as a long term serial monogamist, I’m finding myself making a lot of new choices lately. After an especially rough year, including the death of my father, ending a 3 year relationship with a live-in boyfriend, ending a 10 month relationship with a sleazy dick, getting screwed over by a shady employer, and hitting that “quarter life crisis,” I’m finding myself looking to relationships as less of a solution and more of a diversion.

I’ve made some real progress with not thoughtlessly committing to whomever I’m seeing. I’m really evaluating my needs, wants, and desires. It’s super cool, guys.

There has definitely been no lack of suitors, and they’re all pretty legit dudes. BUT! I realize that I can hold out for the legitest of dudes. You’re a sweet guy who likes Pokemon and wants to cuddle and play video games all day? Cool. Do you have an even keeled nature  and a firm grasp on reality? Nope? Next. You’re ultra intelligent and have a romantic streak? Do you have a job and common decency? Oh…that’s unfortunate. Next!!

I never knew how easy it was to be ok with not being interested in a guy who’s interested in you. This might be the bitchiest statement I’ve ever written in my life, but it’s true and important. This blog is hopefully going to chronicle my adventures in figuring out how to date myself…and cute boys….but not, like, relationship-ing them. 

Wish me luck,

Ann Marie

And on that night, a blog was born

Last summer, when I broke things off with my long-term, live-in boyfriend, I was assured it would be no time at all until I was swept off my feet again. I was assured that if I "put myself out there," I would be greeted with endless eligible bachelors. “Out there” I would find myself invited to dinners and movies and bowling and drinks and yacht parties. After a few weeks of moping and drinking white wine while crying over episodes of The X-Files, I dusted the Dorito from my fingers and took control of the wheel.

I started out the only way I knew how: OkCupid. I had decent luck with OkCupid before, I wasn’t mentally prepared for Tinder, and I had no intention on paying real money to lie about myself online. (Drinks: “Socially.”) OkCupid was the easy, comfortable, obvious choice.

A few months after I left my ex, my roommate and her LTR went their separate ways and she was ready to join me "out there" to meet someone new. In an ideal world, OkCupid would be a supplement to "out there", presuming "out there" is the real world. With that in mind, we mapped out bars where we estimated a high ratio of single dudes, picked out our damned cutest outfits, and ventured out on our first Friday night of mutual singledom. After a few minutes of being “out there” and scoping “out there” out, we were sorely disappointed.

Some preliminary searches of "cute boys in Chicago" and "OK Google: find cute boys near me" were inconclusive. Scouring Yelp reviews for the hot dude factor was a waste. After four bars, numerous complex Google searches, and a five-minute foray into Tinder,

“Where the cute boys at?” was said in exasperation. And with that utterance, the title of this blog was birthed. Right there on the floor of G-Man (where the cute boys were not that evening).

Keeping a weather eye for cuties

Welcome to Where the Cute Boys At, a collaborative effort to document the thrills and spills of Chicago’s casual dating scene. We’ll provide venue reviews, post-date analysis, general observations, and other rants and raves as we see fit. At WTCBA, we promise to withhold the identities of the cute boys and the not-so-cute boys we profile, to refrain from hateful speech, and to keep these posts PG-13 so that you can enjoy them with your mother. 

We hope you laugh. We hope you cry. We hope you find a cute boy.

Best,