About You and a Bit About Me

...and want it to be unforgettable—from the drinks to the vibe—you’re in the right place.

At TIPSSY37, I bring over 14 years of bartending experience and 21 years in hospitality straight to your celebration. Whether you're hosting a cozy get-together or a blowout bash, your guests deserve more than just drinks—they deserve an experience. That’s where I come in.

I’m Cynthia, the hands (and heart) behind the bar. I know what it takes to keep the energy high and your guests happy. I anticipate needs before anyone even asks, serve with genuine warmth, and make sure every detail behind the bar is handled with professionalism and heart. I’ve made a career out of making people feel taken care of—and your event is no exception.

TIPSSY37 was born from a deep love of the party atmosphere, great cocktails, and connecting with people. After years of bartending in Chicago—including at Gilhooley’s in Mt. Greenwood until its closing in 2024—I decided it was time to bring the bar directly to you. No matter the occasion, my goal is to make sure you enjoy the night as much as your guests do.

When I’m not serving up signature cocktails, I’m proudly known as “The Lunch Lady” at a local southside Catholic school—so whether it’s kids or cocktails, service is always at the center of what I do.

Ready to host an event your guests will talk about for months? Let’s make it happen.

I’ll bring the bar—you bring the party.