Accepting the Cocktail Challenge


Once you hear about the Cocktail Challenge, you will want to accept it too.

Tess at happy hourGrowing up, each summer my brother, father and I would go on a challenge of my father’s creation. We had Hotdog Challenges, Pizza Challenges, Burger Challenges, and Fry Challenges, just to name a few.

Along with some cousins, we would load up in the car and take off to find the best hot dog in our hometown. We would go to about five different hotdog places, ordering only one dog at each location. We would cut it into equal pieces and each use our bite to judge on taste, presentation, and overall satisfaction. After doing the same at all five places, we would determine the winning restaurant of our Hotdog Challenge. We would do these randomly throughout the summers and it was a great way to cheaply kill a few hours while beating the Los Angeles heat. If you have kids especially, I would highly recommend it. Some of my favorite childhood memories came from these challenges.

IMG_5323With this in mind, I really shouldn’t have been too surprised to hear that my dad created the Cocktail Challenge. The idea originated after my brother Nick and I had both moved out of the house for college and my parents decided to do something new to combat the empty nest. Basically, one Wednesday in 2014 my dad told my mom as she entered our house from work, “Get ready – we are going out for a Cocktail Challenge” and they have been going every Wednesday since.

Put simply, Wednesday Cocktail Challenge is a way for my parents to go on a weekly date night together. Having been married for over 25 years, they know how important it is to help things fresh and interesting.

Here are the rules:

  • Cocktail Challenge happens on Wednesdays.
  • You must go to a different bar each week.
  • You must order a different cocktail each week.
  • If you go to a restaurant instead of a bar, you must sit at the bar.
  • The chooser of the bar will rotate weekly.

What an inventive thing, huh? Cocktail Challenge provides a great way for my parents to get out of the house together on a weekday and check out some local bars. And Wednesday is the perfect night – who doesn’t need a little midweek pick-me-up? Having never been big drinkers, it has been really fun for them to try everything from Mai Thais to Sidecars and alcoholic milkshakes to $20 shots of tequila (which my mom knocked over and spilled…). They have been able to spend quality time together and explore in a new way the city they have called home for the entirety of their lives.

After going it alone for a few months, the Wednesday Cocktail Challenge group has started to expanding, often including a few close family friends, and now me. I have been tagging along for almost six months now and it has been a great way to develop my relationship with my parents, making things somewhat more peer-like and less parental.


As Cocktail Challenge has progressed over the years, the rules have become, thankfully, less strict. Being that the size of the party has grown, we now sit at a table instead of at the bar, which facilitates some great (and hilarious) conversations. We also now always choose restaurants where we can all enjoy a dinner together, and some times forgo cocktails completely for a beer or wine bar.

It is so nice, and very important, to set aside dedicated time for the people you love. Cocktail Challenge is great for that. It is the same time and day each week, but the variety in venue and cocktails keep things interesting.

We are always sure to capture the cheers!

And sometimes we continue the fun and go for frozen yogurt after, my dad’s favorite.

This weekly ritual has become the best way to experience Los Angeles and spice up my week! I would highly recommend that you follow my father’s footsteps and create a challenge that works for your life! Maybe it is an Exercise Challenge (try one new class at the gym each Monday), a Meet Up Challenge (join a new group on Meet Up weekly), a Dessert Challenge (find the best ice cream and pastries in town), or a Hiking Challenge (pick a new trail every Sunday). The possibilities are endless, but it is a simple way to shake up your daily routine. Like they say, variety is the spice of life!


Will you accept the Cocktail Challenge? Let us know below.



6 thoughts on “Accepting the Cocktail Challenge

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