A Double Date With The Obamas #SouthsideWithYou


“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 hits theaters today and fell in love with my president, first lady, and sweet home 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 drove down in the movie was my block! Shout out to 61st!

For some reason I didn’t want to write a usual review of “Southside With You”. 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 “South Side With You” date, hitting up all the spots Uncle Barry and Aunty Chelle visited on their first date. Ya’ll ready? Let’s go!

The Art Institute of Chicago

The Art Institute of Chicago

The Art Institute of Chicago

The Art Institute of Chicago

It totally makes sense that the POTUS & 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 is a must see. I wonder what was President Obama and Michelle’s favorite exhibit.



President Obama spent his early years in Chicago working as a community organizer in Altgeld Gardens. This is a wall in the “Gardens” that has the name of everyone in the community who has lost their life to gun violence. The Obama’s did not come here on their first date, but it was fictionalized in “Southside With You”, so we decided to include it. Also, I worked in Altgeld Gardens for 3 years and wanted to bring Steve to see the memorial.



The Obama’s 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 theatre 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 Obama’s! 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,


P.S. Special thanks to our little sister Kiera for snapping these pics. You’re the best <3

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