Personalized Dating & Relationship Advice | MyCheekyDate Coaching

Schedule

Sat, 20 Dec, 2025 at 05:00 pm to Tue, 20 Jan, 2026 at 11:30 pm

UTC-08:00

Location

Portland | Portland, OR

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One-on-one dating & relationship coaching from MyCheekyDate – clear, caring advice for modern love that actually works.
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.

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Where is it happening?

Portland, United States

Event Location & Nearby Stays:

Tickets

USD 169.08 to USD 365.13

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