Category Archives: single woes and married foes

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.

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Navigating the Family Wedding.

This coming holiday weekend, I fly to Vail, Colorado for my 2nd cousin’s wedding. She’s 58 years old and this is her first marriage so take note – there’s always hope!

I’m the youngest cousin in the family, aside from my slightly older cousins who have all had babies (seriously, one had 3 in 3 years). They hail from places like Virginia, Texas, and Kansas City. They look at me all judgmental like the crazy city slicker I really am (and sometimes I catch a slight glimmer of jealousy in their eyes).

Much like my family visits at Thanksgiving and Christmas, I’ve been pondering all week about the inevitable question – “So, why didn’t you bring a date to the wedding?” My potential responses are ready to go:

  • “I actually had a male escort on hold a la The Wedding Date but I did a cost-benefit analysis and it turned out the cons outweighed the pros.”
  • “I was online dating in an attempt to meet someone but then my new boss was spotted on Tinder and eHarmony so I had to cease immediately for fear of e-running into him.” (true story)
  • “I’m selfish, I’m fabulous, and I’m single. Get over it.”
  • “Having grown up around this family for the past 28 years, I know better than to bring any man around to you people.”
  • “I’m pretty sure I’ve dated all the eligible men in the westside. I’ve tapped out LA.” (another true story)

Wish me luck!

In Preparation for Christmas.

Unless any of you have acquired a boyfriend over the last 5 weeks (kudos if so!), I felt it appropriate to post a follow-up to In Preparation for Thanksgiving. I am returning to Chicago with a massive cold (not to worry though – the doctor just gave me a bunch of drugs so I should be singing Christmas carols minus the dripping nose in no time) and am fully prepped to answer the following annoying question:

“So, why are you still single?”

I have compiled the following potential responses:

  • “I don’t know; maybe I should stop telling guys on a first date that I have a dating blog.” (just kidding…this is like a 6th date revelation)
  • “I keep meeting these cute guys in Orange County but once I tell them that I voted for Obama, they run away.”
  • “I’m on an airplane and/or in a different city every other weekend. Apparently, most men find this detrimental in dating a person. Me? I think it’s pretty f–king rad.”
  • “I have no idea. Go get me my 5th glass of champagne and let’s sit down for the next 3 hours of this holiday party to talk through all my many single person issues. And no, we’re not spending one minute talking about you.”
  • “I really am holding out for Ryan Gosling. He lives in LA; I live in LA. What – is this not realistic?”
  • “BECAUSE BEING SINGLE IS AWESOME.” (True story. Thanks to my friend D. for that one)

Happy Holidays everybody! To the married folks – I enjoyed all the holiday cards (who doesn’t love snail mail??) and I hope there aren’t too many in-laws and screaming children this Christmas. To the single folks – I hope there are many ugly Christmas sweater parties and drunken makeouts heading your way.