Messy Lola — A Chicago Comedy‑Drama Series About Life, Chaos, and Everything In Between — Begins Episode Rollout in Spring 2026

Cynthia Kaye McWilliams in full “I know you didn’t just email that” mode as Lola—giving face, fashion, and fierce focus on the set of Messy Lola.

Messy jobs, messy friends, messy exes — Messy Lola is the Chicago comedy-drama you didn’t know you needed. Starring Cynthia Kaye McWilliams, this indie series from CynCity Productions drops Feb 2026. Watch, relate, repeat. #messylola #cyncityproductions #cynthiakaymcwilliams #TVseries #indiefilm

Messy Lola, the independent comedy‑drama series from CynCity Productions, is rolling out its season of relatable chaos one episode at a time beginning February 16, 2026. The Chicago‑set show — starring and executive produced by Cynthia Kaye McWilliams — explores the everyday messiness of life in your 30s and 40s, framed through humor, heart, and unfiltered honesty.

A series that celebrates flawed yet lovable humanity, Messy Lola follows Lola — a woman who’s an expert at managing everyone else’s chaos… but not her own. Each episode dives into life’s relatable messes, from workplace scandals to love, self‑discovery and the unpredictable twists of everyday adulthood.

Messy Lola Episode Rollout Schedule

Episode 1 — PilotLola and her friend Sia face a workplace scandal involving inappropriate Zoom chats. To save her job, Lola must do the unthinkable.Available: February 16, 2026

Episode 2 — If It’s Too Good to Be TrueLola impulsively quits her job for a “dream opportunity” that backfires — now she must invent a scheme to get it all back.Available: February 16, 2026

Episode 3 — Third Generation MessAn unexpected visit from Lola’s estranged mother dredges up messy family history.Available: March 2, 2026

Episode 4 — Lola Up in SmokeLove sparks, flares, and fizzles in this quiet, introspective episode about the messy complexity of relationships.Available: March 16, 2026

Episode 5 — Lola In ChargeLola must fire the beloved but accident‑prone receptionist Esther — an awkward yet comedic test of leadership.Available: March 30, 2026

Episode 6 — Dude. Drop. Dismissed.A high‑stakes game night spirals out of control, turning friendly competition into chaos.Available: April 13, 2026

Episode 7 — Lola Finds OutTrapped in a room with Kayla, secrets unravel and threaten Lola’s closest connections.Available: April 27, 2026

Episode 8 — Lola vs. TerranceAn open‑air confrontation with Terrance becomes public spectacle — and even messier.Available: May 11, 2026

Episode 9 — Lola’s Teyhive EmergencyWhen Lola’s babysitter cancels, she must find an unexpected solution — while keeping her big‑ticket concert night alive.Available: May 25, 2026

Episode 10 — Lola Is DoneA cascade of setbacks culminates in a life‑altering moment and a messy decision that might change everything.Available: June 8, 2026

Every emotion. Every episode. Cynthia Kaye McWilliams gives us Messy Lola—because life doesn’t come with a script... just good lighting and a lot of coffee.

A Show for Anyone Who’s Ever Felt “Too Much”

Messy Lola captures the universal truth that life rarely goes as planned — but it’s the detours, mistakes, and detours that make the journey worth telling. Lola’s world is one anyone with ambition, love, anxiety, and friends can recognize — a messy masterpiece of modern adulthood.

Starring Cynthia Kaye McWilliams — beloved for her roles on television and streaming — the series blends comedy and heart in equal measure. Shot entirely on location in Chicago with an all‑Chicago crew and cast, the series is a vibrant ode to the city’s energy and creative spirit.

How to Watch

Released bi‑weekly, Messy Lola episodes will be available for purchase and viewing through the CynCity Productions online platform:👉 www.cyncityproductions.studio/messy‑lola 

About CynCity Productions

Founded by Cynthia Kaye McWilliams, CynCity Productions is a Chicago‑based independent production company reimagining how stories are created, shared, and supported. Built on artistic ownership, mentorship, and community‑centered production models, CynCity champions creative voices and empowers them with equitable opportunities.

Press Contact

Christi Love, With an Eye PR — [email protected]

Leroy Burton, LSB Media — [email protected]

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