Tag Archives: Chicago

How I Learned to Facebook Stalk Part I

Ladies, I don’t have much dating advice. But when I do, I swear by it.

Whenever you meet a guy in a bar/social event/party and hit it off, immediately excuse yourself to the bathroom and find him on Facebook. Allow me to explain…

I met Mr. Cubs Fan at a Cubs bar in the Lower East Side during the 2016 World Series. Like all hopeless Cubs fans, I did not assume this handsome blonde had any interest besides Cubs bar chit chat. However, we spent half of the game chatting about Chicago, our jobs in the technology industry, and he complimented my glasses (because when my job is killing me softly, I wear glasses to bars). To my surprise, he asked for my number and I happily handed it out. He even texted me the next morning saying we should hang out that night.

Thanks to said job, I didn’t get around to checking Mr. Cubs Fan’s Facebook page until later the next day. I noticed 2 blonde boys in his feed and figured those were his nephews. Until I got to his “About” page where his status said “Married”. I immediately found his wife on Facebook and verified he was indeed married to a blonde girl in suburban Chicago with 2 blonde twin boys.

I fumed and decided to wait to call him out if I ever heard from Mr. Cubs Fan again. Sure enough, he did text that evening, leading to this exchange:


Mic drop. I’m done.

Lesson #1: Appreciate the Small Things in Life.

Lesson #1 of the 12 Lessons of Christmas: Appreciate the Small Things in Life.

I spent a week in my hometown of Chicago for Thanksgiving. Then my job told me that I had to spend another week there. So I spent 2 weeks in Chicago where the thermometer stayed around 25 or less (with the exception of one 55 degree day because – hey – that’s the mother f–king Midwest for you).

One weekday night, I walked to a Pilates class after a day that snowed that should have been an easy 10 minute walk. Instead, I almost slipped and fell 6 times on ice because residents in Chicago can’t be bothered to salt the sidewalk*. I actually caught myself slipping on black ice 45 seconds away from my destination.

Lesson of the week: I now fully appreciate the ice-free and danger-free sidewalks of Los Angeles. It is the little things in life.

* oh, you didn’t know that salting the street/sidewalk is a thing?! Go spend 7-10 months in the Midwest and you’ll learn how good we have it in Southern California.

Thanks Mom.

My parents are a bit…how should I put this? Old School.

As in they got married to each other at 20 (her) and 22 (him). My sister got married at 24. So you can imagine how single, down-on-her-luck me looks to this marrying young family. Having courted in the pre-Internet age, they really don’t understand the complexities of dating in the 21st century.

They also have a not-so-secret agenda to convince me to move back to Chicago — cold, gray Chicago where I’m 99% sure I had Seasonal Affective Disorder (look it up, it’s a thing) 9 months of the year.

This means that for my 4-5 visits to Chicago a year (by the way, I think that they should recognize that is a very impressive amount of plane tickets at $200 – $400 a pop), there is usually some dinner party (yes — dinner party. I told you that they are Old School) or event where the goal is to make Chicago seem like the best place ever and I’m missing out on so much. My recent trip to Chicago in October featured such an event.

My father is a member of a prestigious men’s club that hosted a rackets weekend (did you know that rackets is a sport? I bet you didn’t. It is played by the kind of people that only wear LaCoste alligator pants and Ralph Lauren Polo) and my parents insisted that I attend the welcome cocktail party. The only reason I agreed to go was for the free Prosecco.

Having come off some of the roughest few months I’ve ever had in my career, I’m not exactly a delight at small talk these days. It’s hard to smile and say, “yes I enjoy my job of mindlessly entering data into Excel and doing VLookup and Index Margin formulas 8-10 hours a day” and mean it. Hence why on a scale of 1 to 10 in social situations these days, I’m a negative 2. Suffice it to say that Negative 2 me and the arrogant, young rackets players didn’t really hit it off.

At the cocktail party, my mother made sure to introduce me to Rackets Player Paul who was from geographically undesirable Boston. It turns out that Rackets Player Paul actually works in my industry which is unusual to find anywhere. Then Rackets Player Paul went on to tell me that he was walking down the street yesterday and my mom chased him down. She spotted him in his rackets gear and decided to make conversation about the tournament and mentioned that her single daughter from Los Angeles was also in town. Needless to say, I was mortified.

Mom got a stiff talking-to in the elevator from me (of the “stay out of my personal life” variety). She insists to this day that Rackets Player Paul exaggerated the “chasing him down” part. I’m not sure if I should be insulted or delighted that my parents have gotten so worried that they have taken to chasing down men in the streets of Chicago for me. But I guess it’s good that someone is still trying on my behalf.


Here’s a topic that I have not covered too much because my ego hurts too much admitting to it: rejection.

Two weeks ago, I attended a magnificent wedding of a fellow USC alum in Santa Monica and the minute I saw Mr. Best Man at the altar of the Catholic ceremony, I said – HIM. DIBS.

Now it’s not very often that I truly set my mind to something and don’t get it. 25 years ago on a cold January Chicago day, I told my mother that once I was a grown-up, I was moving to a place where I didn’t have to wear a coat (I mean, practicality at its best at age 4). 11 years ago, I walked on USC’s campus and said “Yes, I’m going to attend college here.” One year later, I started my freshman year at USC in the balmy climate of Los Angeles.

In late 2008, at the height of our failing economy, I set my mind to get a job in marketing. Granted, I got it and it sucked the soul out of me for 2.5 years. But I did it.

If the last 5+ years of dating in Southern California have taught me anything, they have taught me humility. Everyone in LA is here to get what they want.

But I digress…

Back to Mr. Best Man.

Mr. Best Man was a  Stanford grad. A former baseball player slash current personal trainer. I couldn’t have asked for a better Saturday Night Random Makeout. The competition consisted of 2 drunk bridesmaids who started at 10 AM and I had the upper sober hand.

The groom was on my side. Two groomsmen made absolutely sure we were introduced. Mr. Best Man and I danced. We took a shot. We sat and had a fun conversation over wedding cake. Then, the wedding party failed to make an after party happen and I found myself outside with a tired Best Man at midnight who just wanted to go to sleep. Alone.

And so I got into a taxi by myself. There are a million excuses for why he didn’t at least for my number but after 14+ years of dating, I know a blow-off when I see one.

The evening was a bit of a blow to my ego. Like I arrogantly said, I’m not very used to not getting what I want. I’m not used to putting myself out there and getting shot down. On top of it, it was the metaphorical nail to the coffin to what’s been a pretty terrible year of dating.

How much more of this can I really take? I’m pretty sure my standards are already dirt-level low (does he at  have a job at Radioshack? Cool! Does he have a college degree? No, but an associate’s degree will do. He lost all his hair? HA we’re only getting older. He’s bald at 30? — Let’s go!).

Go ahead, mock the anonymous blog writer. But I’m just getting real here, guys. How much more rejection and bullshit can we take?

Then there was the time my date ran away from me at the end of the night after walking me to my car. And by “that time”, I mean, last night.

Regardless, all that’s left to do is fill the hole in the ego and soldier on. Because at this point in life, you can’t just roll into a ball in the corner of your bedroom and stop trying. You save that for when you are a 50-year-old spinster with 7 cats.