Kansas City, KS

Date Night at
the Dive Bars

Entertainment options abound at Kansas City, KS watering holes

“Your destination is on the left,” my GPS alerted as I drove through historic Strawberry Hill, an up-and-coming section of Kansas City, KS that boasts some of the most interesting bars, restaurants and clubs in the city. Marveling at the stately Victorian homes and smaller cottages I drove past, I planned to meet Stephen, a tall, dark and bearded sales rep I’d “swiped right” on a few weeks earlier. First dates are always a bit awkward, but first dates in a new city are even more nerve-racking! To top it off, I was also hosting my sister and her husband from Denver. When Stephen and I were planning our date, he insisted I bring them along, as he wanted to show all of us his favorite haunts in Kansas City, KS.

Plan your friends getaway in Kansas City, KS

Cocktails and comedy

We walked into The Mockingbird Lounge, a relatively new place in a mostly residential area, and immediately picked up a hipster vibe that felt modern but intimate. The minimalist décor included long strands of white lights hanging from ceiling to floor along the wall. I found Stephen waiting on one of the high-top bar stools. “You must be Keeley!” he said as we gave each other the obligatory awkward-first-date hug.

I’m a sucker for anything watermelon, but the Huckleberry Lemonade also piqued my interest: blueberry, lemon and vodka sounded like a great combo.

I introduced my sister, Jenna, who smiled and waved, and her husband, Brad, who shook Stephen’s hand forcefully with a sly smirk. I took a seat next to Stephen to browse the impressive craft cocktail menu, which had plenty of tasty options. I’m a sucker for anything watermelon, but the Huckleberry Lemonade also piqued my interest: blueberry, lemon and vodka sounded like a great combo.

“What sounds good to you all?” asked Stephen.

“Watermelon mojito!” I blurted. What can I say, old habits die hard. Jenna admitted she thought that sounded good but she wanted something different, so she went with the Mockingbird Margarita, which has a twist of blackberries and mint.

Meanwhile, Brad and Stephen bro-ed out as they each ordered a Maple Old Fashioned.

“A whiskey drinker—I knew there was something I liked about you!” Brad teased.

After the drinks came, they sounded downright snooty as they marveled that the Old Fashioned was complex, yet refreshing. They said the maple syrup really elevated it so it paired well with the orange bitters. I hadn’t realized my brother-in-law was such a connoisseur.

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Stephen and I perused a collection of party games stacked against a wall but turned around when we heard a mic check. We had arrived in time for weekly comedy night—a nice way to break the ice on a first date. If we’d been there the previous day, we would have played in trivia night. We were excited for the lineup of “Baby Powder,” the Mockingbird’s main comedy showcase. The show is a mix of local talent, with a traveling headlining act. During our chats with fellow patrons, we found out that “Shut Up and Clap” also hosts an open mic night every Thursday for the local comedian network and any interested new members.

After the first comic finished, Stephen suggested we step outside; Jenna and Brad stayed inside for the second act. Stephen led the way out to the lounge’s patio so we could enjoy the fresh summer air. Much to our delight, a happy pup named Finch greeted us. Turns out, he lives upstairs with his owners, who also own the bar. After a few obligatory chin scratches and woojy-woos with the dog, we found a seat at some large wood tables. In that moment, I knew I had fallen in love—with the city view! We could see the whole skyline twinkling across the river.

We began chatting about my move from Denver, Stephen’s love of baseball and our jobs. The longer we talked, I felt more and more at ease and finally mustered up the courage to mention, “I saw on the menu inside that they serve brunch all day long.”

“Well, let’s plan to come back next week, then? Those chorizo waffles sound killer,” Stephen said, smiling. My heart soared in anticipation.


Keep the (pin)ball rolling

Stephen wanted to show us what else Kansas City, KS has to offer. Just around the corner is 403 Club, a fun bar with everything from pinball machines to pool to a hot dog Ferris wheel. We found a casual atmosphere with an eclectic crowd. We immediately gravitated toward the bright lights coming from the back wall, which is lined with colorful pinball machines. Stephen quickly reached into his pocket for a few quarters, pulled a lever and watched the ball fly up the ramp on the “Ghostbusters” game. Hearing the theme song come blasting out made me nostalgic for the times Jenna and I stayed up late watching the movie with our parents on the VCR.

The 403 Club in Kansas City, KS is a fun bar with a wall of pinball machines and everything from pool to a hot dog Ferris wheel.

Jenna and I headed up to the bar. Perusing the selection of more than 60 craft beers, I was pleasantly surprised to see selections from Left Hand Brewing Company as well as Ska Brewing, from my home state of Colorado. One of the bartenders made several suggestions, so I decided to try one of each, opened a tab and headed back to the table. The four of us spent the next hour taking turns on each machine, trying to see who could score the most points. For such “retro” entertainment, the machines seemed really well-maintained. The loser of each game had to buy the next round of beers. I’m pretty sure Stephen, channeling his inner Peter Venkman, let me win most of the games so I didn’t have to pay.

Plan your friends getaway in Kansas City, KS

Diving for a float

When we ran out of quarters, we made our way a couple blocks over to Chicago’s, another hidden gem with an exterior that belies the awesomeness within. We took a seat at the bar and noshed on free popcorn as we caught the end of the Royals game. The bar has a dozen specialty beers on tap, including several made regionally. Stephen had an Alpha Hive IPA, and with the night winding down, I went for the adult-style Root Beer Float, a large-ish shot consisting of beer and root beer Schnapps and topped with Coke—the perfect sweet to top off a sweet night.

Chicago’s Neighborhood Bar in Kansas City, KS has a dozen speciality beers on tap, including several made regionally.

At the end of the evening, Stephen took my hand as we all walked back to our cars, which were parked near where our night began. As we strolled, still buzzing from the electricity of an evening well-spent—and let’s face it, the drinks we’d consumed—we all agreed none of us should be driving. When we got to the cars, Stephen pulled out his phone and summoned an Uber for himself and a Lyft for my guests and me, since he couldn’t have two cars come at the same time from the same company. When our car arrived, he opened my car door for me, and we bid each other good night and went our separate ways. I couldn’t take the smile off my face the entire ride home. It was the perfect first date. I couldn’t wait to see Stephen again and see what else Kansas City, KS has to offer.

Plan your friends getaway to Kansas City, KS.