Tag Archives: dating

Lesson #9: Don’t Be Afraid to Laugh at Yourself.

Christmas Lesson #9: Don’t Be Afraid to Laugh at Yourself

There were a few moments this year when my friends would bring up my embarrassing dating stories and I’d turn bright red and get angry. Sometimes hearing the sentence, “Remember when you dated the vegetarian who insisted on going to restaurants to share plates and didn’t let you eat meat dishes?” or “Why did you stay on that drinks date where Sober Joe invited you for a drink and then he drank iced tea while you had your 2nd Chardonnay?”  just completely rubbed me the wrong way. Then, I realized they bring up those stories because they are just so memorable and entertaining that the stories stuck with them. And that I should really lighten up.

Recently, on a chilly Friday morning, I found myself on a corner in Brentwood next to Mr. High Maintenance. I only noticed him because I thought it was strange that guy was wearing sandals, shorts, and a tank top when it was 50 degrees outside. Then we each did a double-take and I realized it was the Pellegrino and Sauvignon Blanc-swigging prima donna himself (in fact, he was holding 2 bottles of Pellegrino). He looked at me and ran across the busy street, straight into incoming traffic.

He didn’t get hit by a car and I fought the urge to shout, “Hey —, good to see you! Maybe you should put on some pants. It’s cold out here.” Then I promptly burst into laughter. The men of LA that I have dated literally run into incoming cars to get away from me. And that’s hilarious.

5 Reasons Why I’m a Bad Date.

We know I spend a lot of time here complaining about the men of Los Angeles. But I’m willing to admit the common thread among the ones I’ve dated was obviously me. Which begs the question – what exactly am I doing wrong in the dating game?

1) Things in my life have been difficult lately, especially work-wise. Sometimes, it’s hard to keep these complaints to myself. Maybe it’s time to acknowledge most people are very stressed about their jobs and to keep my frustrated thoughts to myself until date three or fifteen. You know who someone doesn’t want to date? Debbie Downer.

2) When I actually really, truly like a guy, I get awkward. Like spaz city awkward in front of him. Revert back to 5th grade (mouth chock full of braces, chubby red cheeks, and monster eyeglasses) awkward. I can see why this has frightened some Prince Charmings away.

3) I’ll admit it – I have some commitment issues. Signing a year-long lease on an apartment gives me hives. I don’t like to plan vacations more than 2 months in advance (and even that seems a little close…who knows what could change in my life? But guess what — life will be exactly the same in 2 months!!).

4) I have a short attention span. The minute the conversation turns to minute sports details I don’t know, I start to wonder “If I get home in 45 minutes, I can catch The Walking Dead on my DVR before it’s past my nerd alert bedtime…”

And finally…

5) I keep an online dating blog and karma is simply biting me in the ass.

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.