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.