A few weekends ago, I packed my bags and headed to Chicago with my friends Annabelle and Meagan for a very special reason — the live show of their podcast, Adderall & Compliments. If you’ve listened before, you already know the magic these two bring to their community, but seeing it unfold in real life was something I’ll never forget.
I’ve been helping the girls behind the scenes for the past few months, and it’s been one of the most rewarding experiences. What drew me in is the way they’ve built such a deeply supportive and open space for their listeners — lovingly called “kittens.” Their honesty about mental health, the ups and downs of life, and the messy, unfiltered truths have touched people far beyond what you’d expect from a comedy-meets-pop-culture podcast.
At every live show, I watch as kittens come up to Annabelle and Meagan with tears in their eyes, sharing how the podcast changed their lives. Many talk about finally feeling understood, about no longer feeling so alone in their struggles. Some even admit that during their darkest moments, listening kept them tethered to hope until they were able to reach out for help. Hearing those stories firsthand is both humbling and powerful — it’s a reminder of how important their work really is. This is so much more than entertainment; it’s connection, healing, and community.
And that’s why I’ve been traveling with them for these shows. Supporting their mission feels like the most natural thing in the world.
Falling for Chicago (All Over Again)
Beyond the live show, Chicago itself made the weekend unforgettable. I have to say — I seriously wish I could hop on a plane right now and be back in that city. If you’ve never been, add it to your list immediately. It’s one of those rare places that manages to be vibrant yet welcoming, urban yet surprisingly clean, and filled with incredible food, endless shopping, and — not to be overlooked — charming Midwestern men.
My first trip to Chicago was about seven years ago for a professional conference, and I still remember the moment I fell in love with it. Yet somehow, even after a handful of visits, there are still so many landmarks I haven’t crossed off my list. (If you’re looking for insider tips, I highly recommend checking out Gisele Chic’s local guide — it’s fantastic.)
Our Stay on the Lake
This time, we checked into the W Hotel Lakeshore on Thursday night, and let me just say — the view alone was worth the trip. Our room overlooked Lake Michigan, that brilliant stretch of bright blue water that could easily trick you into thinking you’re staring out at the ocean. I remember being totally confused the first time I saw it years ago — a massive lake with waves? But now, I just find it mesmerizing.
There’s something about waking up to that sparkling water outside your window that makes everything feel a little more special.
A Friday of Fun (and Good Hair Days)
By Friday morning, we were ready for a little pampering before the show festivities. Naturally, that meant a trip to Drybar in River North for blowouts. I don’t know what it is about Chicago, but getting your hair done there feels like part of the experience — as if you’re gearing up not just for a night out but for the city itself. With our curls bouncing and spirits high, the weekend was officially in full swing.
The Bigger Picture
Looking back, this trip was so much more than a weekend getaway. Yes, it was about Chicago — the food, the shopping, the hotel views. But at its heart, it was about being part of something meaningful: supporting Annabelle and Meagan as they share their voices and stories with the world.
It’s easy to underestimate the power of a podcast or a community built online, but watching the kittens connect in person showed me how real and profound it is. These shows are about laughter and fun, yes, but also about creating a space where people feel seen, valued, and understood.
And to me, that’s priceless.
Final Thoughts
As I sit here reminiscing, I can’t help but feel grateful — for the chance to travel with friends, for the beauty of a city like Chicago, and most of all, for the reminder that connection truly matters. Whether it’s through a podcast episode, a hug at a live show, or a simple conversation, the ripple effect is real.
So here’s to more weekends like this one — filled with good friends, good cities, and communities that remind us we’re never really alone.
