I am not the originator of this idea, but I have an amazing friend who asked me to do this with her a Very Long Time ago. I think I was 22 years old and it was her life that needed the shake-up, but I was a willing partner-in-crime.
Dressing up and doing our makeup differently had us feeling like new characters in our lives. Like permission to be someone just a little different for a night, we went to a restaurant new to us both and ate and drank things we'd never normally order. And then came a life-changing decision. We were on the corner of Wooster & Grand Streets in NYC with three bars facing us. I'd been to the one on the left; she'd been to the one on the right. On a "New Night", the choice is clear — we had to go to the one in the middle, Toad Hall. Unbeknownst to us, Toad Hall is a favorite neighborhood spot to play pool. The back area

was filled with serious poll players — all men — ranging in age from 30 to 70, from every walk of life. We were at the part of the night where we were looking for the things we'd never done. (That guy over there chewing tobacco, yup, had to ask him for some to try. So that was the first, and last, time I chewed tobacco.)
Sitting on the bench, I realized I'd never written my name on a "Pool List" at a bar before. I wasn't great at pool, and clearly, this was a pool-playing crowd, so I was more than slightly intimidated, but I had to do it anyway. We both did.
When it was my turn to play, I politely explained to my opponent (who was clearly about to kick my ass in pool), that we were on a "New Night" and I did not know what I was doing. I remember everything about this lovely gentleman. He was a psychotherapist, probably about 65 years old and he absolutely loved the concept of our "New Night" — and he decide he was going to teach me how to play.
And he did. And I showed up every night for the next month to keep learning from him. I got good enough that I decided to brave playing pool in my own neighborhood at the old biker bar, The Racoon Lodge, on the Upper West Side. This was a serious pool playing bar.

The next part of the story spans over ten years, so I'll spare you a lot of the details. Suffice to say, I got so addicted to playing pool in my early 20s that I'd call the bar to have someone put my name on the list before I left work, so by the time I got home, changed and ran across the street, it'd be my turn to play. When I inevitably lost after a few rounds, I'd put my name back up and run across the street to the Alligator Alley where they wait wasn't so long, and practice there before running back for my turn at The Lodge.

I met countless people who affected my life in those bars. I could dedicate a blog post to each and every one of them and just how far the ripples went affecting all of our lives. But the real story is when I came back to The Racoon Lodge after returning to NYC from living in Montana for 7 years.
One Sunday afternoon, I had a day there where I played pool like the gods themselves were controlling my shots. I beat everyone that day and it didn't go unnoticed.
A woman approached me and asked if I'd join her pool team. I explained I didn't usually play this well, but she said that was ok and I should show up on Tuesday night. She wouldn't be there, but would "tell the guys I'm coming."
Come Tuesday night, I didn't want to go. It was a blizzard that night so I had a reasonably goo excuse to stay on the couch and I almost did. But I had to reinvent my life in New York. I'd gotten divorced 2 years prior and spent most of my free time traveling back to Montana or Alaska, half pretending my life was still out west. So I went.

And that is where I met my husband. He was the co-captain of the team and when I saw him sitting in the booth with his clipboard, waiting for his new player to show up, I had that voice in my head quietly say "There he is."
We've been married almost 20 years now and have two kids. And I am telling you with 100% certainty, if my friend hadn't asked me to have a New Night with her when I was a mere 22, I would have a completely different life.
You may not need that big of a shake up, but if you're looking for something and can't quite figure out what it is; a New Night may be just the trick.
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