Chicago Style Love; How to Recreate the Obama’s First Date

BY: - 31 Aug '16 | Marriage

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“On our first date, I treated her to the finest ice cream Baskin-Robbins had to offer, our dinner table doubling as the curb. I kissed her, and it tasted like chocolate.” -Pres. Barack Obama

Last week, I had a chance to check out Southside With You, which was released in theaters last weekend. After watching it, I fell in love with my president, first lady and sweet home of Chicago all over again. Written and directed by Richard Tanne, the film tells the story of the Obama’s first date on the Southside of Chicago.

I thoroughly enjoyed seeing Southside With You. It’s evident Richard Tanne and his team took their time to research how Chicago played a third party in the Obama’s love story. Plus, it’s always fun to see your city in a different light. Also, the first street Barack Obama drove down in the movie was my block! Shout out to 61st!

I wanted to show my appreciation for the movie, but I didn’t want to do a review. I wanted to do something different. Something special. I literally prayed about it, lol, and it came to me: My husband and I would go on our own Southside With You date, hitting up all the spots Uncle Barry and Auntie ‘Chelle visited on their first date. Ya’ll ready? Let’s go!



It totally makes sense that the POTUS and FLOTUS went to the Art Institute of Chicago on their first date. Steve and I had a chance to check out their Gordon Parks exhibit, which was a must see. I wonder what President Obama and Michelle’s favorite exhibit was.



President Obama spent his early years in Chicago working as a community organizer in Altgeld Gardens, a Chicago public housing project. There is a wall in the “Gardens” that has the names of everyone in the community who has lost their life to gun violence. Though the real Obamas did not come here on their first date, the wall scene was fictionalized in Southside With You. So we decided to include it. Also, I worked in Altgeld Gardens for three years and wanted to bring Steve to see the memorial.



The Obamas went to the movies on their first date to see Spike Lee’s Do The Right Thing. Seriously, I LOVE them. The movie isn’t in theaters anymore, so we brought the theater to us.


It’s always a good sign that a date went well if you end with ice cream. Steve and I went to the same Baskin Robbins they went to and got a chocolate ice cream cone. There’s actually a plaque on 53rd Dorchester in Hyde Park, at the very spot where Barack and Michelle had their first kiss. Delicious.


This date was fun, but something was missing… The Obamas! Hey, President Obama and First Lady Michelle, we would LOVE to go on a Southside WIth You date with you two. Ice cream on us?

Love Always,


BMWK, what are the most romantic venues to visit in your hometown?

About the author

Nikki Carpenter wrote 46 articles on this blog.

Nikki Carpenter, also known as Nikki and The City, is an urban media expert from Chicago who loves to travel and report on issues that impact different cultures and communities. Nikki's work has been featured on Huff Post LIVE, Jet Magazine, and ESSENCE just to name a few.


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