I Went On 30 Dates In 30 Days. Here’s What I Learned

I dated lawyers, (wannabe) rappers and conspiracist theorists—and saw today’s hottest new artists.


Every night in November around 9 pm, my phone buzzed with a message saying my car was outside. It was a nightly reminder to swallow my anxiety, to muster every last molecule of energy I had, and force myself out the door.

“You ready?” my driver would ask.

“Yes!” I’d say, though my stomach twisted into a million knots as soon as they hit the gas pedal.

When I first told people I was going on a new date to a new concert every night of the month, they told me I was insane.

As an introverted, chronically single 25-year-old in Chicago, I wanted to challenge myself. To get out of my comfort zone. To meet new people. To actively date for a month (instead of just going to a bar with my friends and giving judgy looks to any guy who tried to approach us.)  

I wanted to see what it’d be like to take a guy on Tinder seriously, instead of just trolling him with Beyonce GIFs.

Collaborating with Red Bull Sound Select on a project called 30 Dates In Chicago, I was given two tickets to each show in their November concert series, “30 Days In Chicago.”

Each night I brought a different date, snapped a picture with them and asked them their most random personal fact, which was featured on Instagram along with some footage of each concert. The experience included a ride in a Red Bull-stocked Volkswagen Atlas to and from each show.

Going on 30 dates in 30 days was insane. But it let me meet strangers, flirt with crushes both old and new, and see artists on the verge of superstardom like Migos, Kehlani, and Noname (often with VIP seats. Thanks, Red Bull and Grandstand!)

But it wasn’t just about taking chances. It was about giving them, to guys I once would have dismissed for not being good enough (or Harry Styles).

At the end of my 30 dates, I didn’t find love. I didn’t find a soulmate. I didn’t even have a “Princess Diaries”-style foot-popping kiss. But I built meaningful personal connections with a lot of people I never would have gotten to know otherwise. I reunited with people from my past. I had some second dates, and even a few third dates.

And I learned a lot.

For example:

– Don’t show up to dates on time–no one does that. Arriving 20 minutes late is the new “being on time.”

– Forget Tinder and Bumble. The way to snag a date is to walk up to them in person and ask. It sounds old-fashioned, it sounds scary AF. But if I, the queen of awkward can do it, you can too.  You’d be surprised how many people are receptive to it.

– If a guy makes you say a prayer with them on the first date, don’t make a joke about how you’re grateful for French fries. (Yep, this happened. More on this later.)

– People don’t have their shit together, even if they look like they do. I went on dates with artists, insurance agents, rappers and lawyers–all of whom I’d either met on Tinder or been set up with (by friends, or even by my own step-mom). I noticed that we’re all in the same boat. No matter how flashy someone’s Instagram feed is, they’re probably just as insecure as you. If I opened up about my anxieties and weaknesses, my date would, too. Even if they were a high-powered lawyer. And that was incredibly refreshing.  

– You’d be surprised how much you have in common with people who appear to be totally different than you. Once the lawyer and I got through small talk about Star Wars (which I know nothing about) and my guilty Kardashian obsession (which he seemed horrified by), we laughed about random things like wanting superpowers as kids. He even told me he wrote a 75-page honors essay about Batman.

– If you’re looking to fill awkward silence, talk about food. I had so many conversations about the best way to eat potatoes (mashed, obvi).

– Be nice to people. You never know how they might come back into your life, often for the better: One of my dates helped me find a gallery space for my pop-up bar’s first event. Another date scored me a feature in a hip-hop blog.

– Don’t drink tequila-pineapple Red Bulls six days in a row. On the seventh day, you’ll wake up with the shakes and want to totally stop dating. During my first week, I consistently used alcohol as a social crutch. I was forced to take a morning off work because I wasn’t taking care of myself. When you suffer from social anxiety like me, it’s so easy to turn to alcohol to make conversation easier. After getting the shakes, I went to a concert totally sober and had one of the best conversations of the whole month. TLDR: The more you keep forcing yourself to date, the easier the conversations will get and you won’t be so dependent on liquid courage.

– Dating is something you can control, but having chemistry with someone isn’t. You can put yourself out there every day, but when you have a “spark” with somebody, you’ll know instantly.

Here’s a sampling of my most colorful dates (both good and bad):  

Most Likely To Be A Christian Rapper: #1

Not only did my first date of the month pray at dinner before the show, he made me say what I was grateful for before I was allowed to eat my fries. This guy had grown up without a TV, in a conservative Christian home, went to a Christian school from kindergarten through college. At college, he got interested in rap music and started writing verses for fun. His raps have clean lyrics (so his parents can listen!), but that didn’t stop him from belting out every word to Young Thug while jumping around like a hot potato.

Most Spontaneously Fun: #3

If I were on a blind date and was thrown into a social situation with people I’ve never met, I might freak out. I thought we were going out to dinner and drinks just the two of us courtesy of Red Bull, but when we showed up to the restaurant, the whole Red Bull crew was there to greet us. Instead of having a panic attack, my date was super chill about it. We ate a ton of good food. Plus, he’s a fan of Blow Pops and Kehlani, so he’s a winner in my book.

Most Likely To Get Kicked Out Of A Concert: #12

Imagine going to a small show on a Sunday night at a quiet, intimate venue. Sabrina Claudio blesses the stage with her moody aesthetic and soulful voice, and while everyone else respectfully claps after her songs, your date hoots and hollers like a motherf**ing chicken.

Funniest Date: #19

Not only did #19 love Lizzo’s girl-power anthems and twerk-filled dancing, but I laughed the most on this date. We talked about everything random-from how he got drunk for the first time at age three (he told me he mistook a pitcher of cocktails for cherry juice) to how he eats two or three jars of crunchy peanut butter a week. Yep, he spoons it straight from the jar, and I’m seriously impressed (but also a little concerned for his health?!).

Most Polite Date: #14

Being short at concerts isn’t an ideal scenario, but this guy cleared a path for me to make sure I could see at all times. He also thanked me for bringing him at least five times and genuinely listened when I talked about all the food I was planning to stuff my face with on Thanksgiving. A+.

Most Disappointing Date: #10

One of my crushes was a guitar player I see regularly at a jam night I go to, which is held by Chance the Rapper’s drummer, Stix. After one such jam night, I walked up to him and asked him out, something I’ve never done in my life before. He said yes, and I was incredibly excited, imagining us flirtatiously bantering about Kanye albums together. Instead, we talked about the different drugs he’s done (which of course, I’m not judging, but weird to bring up within the first five minutes of conversation?) and what an awesome drunk driver he is. Cool, bro.

Most Likely To End Up In My Burn Book:  #30

When a first date lasts for more than six hours, and includes spazzily dancing at the Migos and Lil Yachty concert together, it’s a good sign. I can barely spend six hours with people I like. It’s also probably a good sign when your date texts you every night afterwards, about random things like “Riverdale” or his newfound love of sundried tomatoes (wtf?). So when they not only agree to help you on an event you’re planning, but volunteer to photograph it for you, you’d think they’d stick to their word. Well, that’s what I get for trusting someone who lives with his mom, does “business” overseas and had a radio show about conspiracy theories. This man showed up an hour-and-a-half late to my event with what I’m now convinced was a toy camera. When I asked about getting the photos after the event, he changed the subject. When I asked again, he started replying to texts 10 hours later, until one day he never texted me back. Seriously, if this dude can’t email a few digital photos or bother to trim his hair, he sure as hell can’t be trusted with anything else. Boy, bye.

Most Fate-Driven: #s 11 & 29

On a Thursday night a year-and-a-half ago, some coworkers and I went to a divey karaoke bar after happy hour. Had I not stayed for an extra round (which I certainly didn’t need), I never would have met Jeremiah. We exchanged numbers, but I didn’t see him again after our drunken night of talking about Chicago hip-hop. That is, until he became my 29th date this past November. We had kept up with each other on social media (read: occasionally liking each other’s pictures) but it was great to connect on a deeper level and actually get to know each other.

Before 30 Dates started, when I was scrambling to update my Tinder profile, Jeremiah also mentioned he had a friend who was interested in going to a concert with me, and I still needed dates.

His friend ended up being someone I went to high school with. (Talk about random.) Like most people, I try to block out those four years of my life, but I agreed to go on the date for the sake of the story. Within the first 15 minutes, I could feel my defenses slowly coming down. My former high-school classmate was cool! I gave myself permission to just like him, to stop trying to prove all the “great things” I’ve done since high school, a trap most people fall into when seeing ghosts of peers past.

Having nothing to prove and feeling no pressure made it one of the most fun dates of the month, and it got me thinking—had I never gotten in touch with Jeremiah, had I never stayed an extra half hour in the karaoke bar that one night, I never would have reconnected with Tyler either.

Moral of the story? Say yes to new experiences, take chances, be open to new people and date beyond “your type”—you may surprise yourself with who you actually like. Even if you don’t end up “dating,” making personal connections is worth it, and more valuable than you might think. 

And, always carry hand sanitizer, in case your date sneezes on you in the middle of a concert.

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