Find Clarity in Love | Relationship Coaching & Advice Packages

Dating is hard — we all know this. It can be fraught with self-doubt, rejection, and insecurity. Whether you’re new to dating, returning after time away, or seeking clarity in a long-term relationship, we can help. Our approach is refreshingly simple: practical advice for one of life’s most complicated topics — love.

Backed by over 18 years of matchmaking expertise, the MyCheekyDate team understands first-hand the challenges modern daters face. Having worked with hundreds of thousands of singles across the globe, we bring insight, empathy, and actionable tools to every session. Our goal: to help you build confidence, communication, and lasting connection — both online and off.

Perfect for singles re-entering the dating world or launching a new online profile. Includes a comprehensive review of your dating apps and social media, personalized appearance feedback, and profile optimization tips to help you stand out and attract genuine interest.

Designed for those who connect easily but struggle to take things to the next level. We’ll explore your dating approach, communication style, and challenges in moving relationships forward. Optional inclusion of Profile Me! insights plus advice on tone, texting, and how to express interest effectively — online or in person.

Ideal for daters in exclusive or long-term relationships seeking clarity, better communication, or renewed connection. Work one-on-one with our advisors to build stronger relationship habits, resolve recurring issues, and rediscover the spark that started it all. Hours may also be used flexibly across other packages if preferred.

Simply select the package that best fits your needs, and one of our advisors will contact you to schedule your session. We offer secure online consultations and phone appointments — whichever you prefer. Every session is completely personalized, because no two daters are alike.

MyCheekyAdvice was created from 18 years of dating and matchmaking experience at MyCheekyDate. We’ve helped hundreds of thousands of singles and couples build real, lasting connections. From profile polish to relationship growth, our advice is personal, practical, and refreshingly real.

MyCheekyDate is one of the world’s leading speed-dating and matchmaking companies — hosting events in 50+ cities for over 18 years. Through MyCheekyAdvice, we bring that same warmth and expertise to one-on-one coaching, helping daters navigate everything from first dates to lifelong relationships.

Event Venue & Nearby Stays

Chicago, United States

Concerts, fests, parties, meetups - all the happenings, one place.

Get App