Advice Simplified | Relationship Coaching by MyCheekyDate

Schedule

Sat, 22 Nov, 2025 at 10:00 pm to Thu, 18 Dec, 2025 at 11:30 pm

UTC-06:00

Location

Chicago | Chicago, IL

Advertisement
Real-world dating & relationship insight from the experts behind MyCheekyDate — personalized, practical, and designed for real results.
About this Event

Simplifying the Complicated

Let’s be honest — dating can be complicated. From the first swipe to the first serious talk, it’s easy to second-guess yourself. Whether you’re new to the dating scene, getting back out there, or already in a relationship that needs a tune-up, we’re here to help. Our mission? To make dating and relationships feel less stressful and a whole lot clearer.


Why MyCheekyAdvice Works

With over 18 years of global matchmaking experience, our MyCheekyDate team has spent nearly two decades helping singles and couples connect, communicate, and grow. We’ve seen it all — from nervous first dates to long-term relationship wins — and we know what it takes to find confidence, build connection, and stay true to yourself along the way.


Coaching Packages
Profile Me! — $159 (90 min)

New to dating or re-entering the scene? This session helps you fine-tune your online presence and presentation. From photo selection to profile writing and overall impression, we’ll guide you through small changes that can make a big difference. Expect hands-on advice to help your dating apps and social profiles reflect your most authentic, attractive self.


All About Me! — $295 (3 hrs)

If your connections often lose momentum or never seem to progress, this package is for you. Together, we’ll analyze your dating approach, communication style, and relationship mindset. You’ll receive feedback, actionable insight, and practical strategies for expressing yourself effectively — online, over text, and in person — so genuine connections can finally grow.


Relationship Me! — $345 (4 hrs)

For those in committed relationships or seeking clarity about the one they’re in, this package offers deep insight and direction. Learn how to navigate relationship challenges, improve communication, and reignite emotional connection. Many clients also use these sessions for extra time on Profile Me! or All About Me! packages as they continue to grow and evolve.


What to Expect

Choose the package that speaks to your goals, and we’ll reach out to coordinate your session. Consultations can take place over the phone or via our secure online platform — whichever makes you feel most comfortable. Every coaching experience is personalized to fit you — no cookie-cutter advice, no judgment, just clarity and care.


Experience That Makes a Difference

MyCheekyAdvice was built from 18 years of matchmaking and relationship coaching expertise. Having worked with hundreds of thousands of singles, we’ve learned that dating success comes from authenticity, self-awareness, and the right guidance at the right time. Whether you’re writing your first profile or navigating a lifelong commitment, we’ll help you move forward with confidence and charm.


Organizer Bio


MyCheekyDate is a global leader in speed dating and matchmaking, hosting curated events in more than 50 cities worldwide. Through MyCheekyAdvice, we extend that experience to personalized coaching — helping daters and couples create stronger, happier, and more authentic relationships.

Advertisement

Where is it happening?

Chicago, United States

Event Location & Nearby Stays:

Tickets

USD 169.08 to USD 365.13

Icon
Know what’s Happening Next — before everyone else does.
SpeedChicago Advice

Host or Publisher SpeedChicago Advice

Ask AI if this event suits you:

Discover More Events in Chicago

BYOB Painting Event: OPEN STUDIO
Tue, 02 Dec at 12:00 pm BYOB Painting Event: OPEN STUDIO

Sip & Paint

ART FINE-ARTS
Pre-Shift: A wine tasting for wine professionals
Tue, 02 Dec at 02:00 pm Pre-Shift: A wine tasting for wine professionals

Rogers Park Social

WINE-TASTING FOOD-DRINKS
Chicagoland Industrial Retention Network | December 2025 Convening
Tue, 02 Dec at 02:30 pm Chicagoland Industrial Retention Network | December 2025 Convening

222 W Merchandise Mart Plaza suite 633

WORKSHOPS MEETUPS
Three Cities Social Club - Wicker Park Open House
Tue, 02 Dec at 03:00 pm Three Cities Social Club - Wicker Park Open House

Three Cities Social Club - Wicker Park

Augmented Intelligence: Dr. John Whyte on the Next Era of Digital Health
Tue, 02 Dec at 03:30 pm Augmented Intelligence: Dr. John Whyte on the Next Era of Digital Health

222 W Merchandise Mart Plaza

HEALTH-WELLNESS BUSINESS
Event: Building Agentic Workforce: Microsoft Copilot & Azure
Tue, 02 Dec at 03:30 pm Event: Building Agentic Workforce: Microsoft Copilot & Azure

Microsoft Midwest District

Amit Chaudhuri - "Incompleteness"
Tue, 02 Dec at 04:00 pm Amit Chaudhuri - "Incompleteness"

5751 S Woodlawn Ave, Chicago, IL, United States, Illinois 60637

ART LITERARY-ART
Advanced Garment Creation 101 [December Session]
Tue, 02 Dec at 04:00 pm Advanced Garment Creation 101 [December Session]

FashionBar Headquarters

WORKSHOPS MUSIC
Chicago Singles Bar Crawl - Welcome Shots at Every Bar!
Sat, 23 Sep at 09:00 pm Chicago Singles Bar Crawl - Welcome Shots at Every Bar!

Wrigleyville's BEST Bars TBA (Check your email before the crawl for full schedule!)

PARTIES ENTERTAINMENT
INDULGE CHICAGO
Thu, 16 May at 06:30 pm INDULGE CHICAGO

Chicago

SINGLES-PARTIES ENTERTAINMENT
Love Is Blind! Speed Dating & Candle Making Experience - #BLACKLOVEEDITION
Wed, 28 May at 07:00 pm Love Is Blind! Speed Dating & Candle Making Experience - #BLACKLOVEEDITION

3414 W Foster Ave

WORKSHOPS SPEED-DATING
Pop the Balloon Speed Dating [Vendors Welcome]
Wed, 20 Aug at 07:00 pm Pop the Balloon Speed Dating [Vendors Welcome]

Chicago

Chicago Blind Date Matchmaking and Membership
Thu, 13 Nov at 05:30 pm Chicago Blind Date Matchmaking and Membership

Chicago

SPEED-DATING MEETUPS
Advice Simplified | Relationship Coaching by MyCheekyDate
Sat, 22 Nov at 10:00 pm Advice Simplified | Relationship Coaching by MyCheekyDate

Chicago

SPEED-DATING
Modern Dating Made Easy  | Coaching & Advice by MyCheekyDate
Sat, 22 Nov at 10:00 pm Modern Dating Made Easy | Coaching & Advice by MyCheekyDate

Chicago

SPEED-DATING
Personalized Dating & Relationship Advice  | MyCheekyDate Coaching
Sat, 22 Nov at 10:00 pm Personalized Dating & Relationship Advice | MyCheekyDate Coaching

Chicago

SPEED-DATING
Meet IRL | Curated Speed Dating at Solemn Oath | mid 30s to 40s
Tue, 02 Dec at 06:30 pm Meet IRL | Curated Speed Dating at Solemn Oath | mid 30s to 40s

Solemn Oath Brewery Still Life

SPEED-DATING MEETUPS
SPEED DATING POP-UP Hosted by Single N Minglin
Thu, 04 Dec at 07:00 am SPEED DATING POP-UP Hosted by Single N Minglin

1413 N Ashland Ave

POP-UPS SPEED-DATING
Meet IRL | Curated Speed Dating at Hopsmith  | for singles in their 30s
Thu, 04 Dec at 06:30 pm Meet IRL | Curated Speed Dating at Hopsmith | for singles in their 30s

Hopsmith Chicago

SPEED-DATING MEETUPS
Singles Ages 20s & 30s - Speed Dating -  Chicago, IL
Thu, 04 Dec at 07:00 pm Singles Ages 20s & 30s - Speed Dating - Chicago, IL

Moretti's Ristorante & Pizzeria EP

SPEED-DATING MEETUPS

What's Happening Next in Chicago?

Discover Chicago Events