Three Tips for Going on a Date with Yourself

Friday afternoon when I checked my email, I saw that my very very favorite jazz musician, Robert Glasper, was in Chicago playing at Jazz Showcase – an amazing, iconic jazz club which just happens to be in my neighborhood. I love the whole vibe of the club from the red velvet curtains on the stage, to the framed photos of the who’s who in the jazz world to the sound of martini shakers coming from behind the bar. Everyone who is anyone in jazz has played there over the years. The club was founded in 1947 by Joe Segal who still opens each evening with a welcome message and a pitch for their upcoming concerts. When you are at Jazz Showcase you feel like you are somewhere special. Really special.

I quickly bought an online ticket to the 8:00 PM set. Last year when Mr. Glasper was in town every single show was sold out. I was lucky enough to get in but had to stand the entire concert (which was worth it – and I wrote about it then). This time I was going to have a seat.

What’s notable about this whole experience is that I didn’t even think about inviting someone to join me. Granted, it would have been extremely last minute, but I wanted to go and I wanted to make sure I got a seat. It was spontaneous. It was a weekend night. But I didn’t have plans so I went for it. I took myself out to hear some jazz. I was taking myself out on a date!

I arrived a bit early and took at seat at the corner of the bar with a birds-eye view of the stage. The bartender said “best seat in the house” as he poured me a glass of wine. I slowly sipped and settled into the comfort of my chair. The room filled with fellow jazz aficionados and the energy changed from static to active. I had my iPhone with me, but resisted the temptation to check my Instagram or email. I took the time to people watch. I took the time to breathe.

Robert Glasper and his Trio did not disappoint. And as the set was drawing to a close, Mr. Segal announced that we were welcome to stay for the second set without an additional charge. I was getting tired, but quickly rallied with this opportunity. And I had a lovely chat with a woman sitting next to me between sets –  an artist who was living in Italy but also had a home in Chicago. Learning about her life was as inspiring as the music. And I had the opportunity to say hello to Robert Glasper and tell him how much his music means to me. It was such a perfect evening.

Some tips for taking yourself on a date:

1. Two drink maximum. You are by yourself and you don’t want to loose your inhibitions and do something stupid. I had two glasses of wine and switched to club soda. It was enough to feel relaxed and celebratory but not too much.
2. Be present. Don’t engage with your phone. Look around. Take in the atmosphere.
3. Smile. Sit up straight. Be confident. Even though your goal for the evening is to enjoy by yourself, you never know who you might meet. Could be another woman with an inspiring story, it could be a nice chat with the bartender or you could meet a lovely new man. The possibilities are endless.

Start planning your next date now. Take yourself out for the evening. Have fun!

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