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-05:00

Location

Boston | Boston, MA

Advertisement
Personalized dating & relationship coaching from MyCheekyDate — real guidance to boost confidence, connection & clarity.
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?

Boston, United States

Event Location & Nearby Stays:

Tickets

USD 169.08 to USD 365.13

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

Host or Publisher SpeedBoston Advice

Ask AI if this event suits you:

Discover More Events in Boston

Boston Ballet
Tue, 16 Dec at 07:30 pm Boston Ballet

Citizens Bank Opera House

Grand Kyiv Ballet: The Nutcracker
Tue, 16 Dec at 07:30 pm Grand Kyiv Ballet: The Nutcracker

Citizens Bank Opera House

PERFORMANCES ENTERTAINMENT
A Very Motown Christmas at City Winery - Boston
Tue, 16 Dec at 07:30 pm A Very Motown Christmas at City Winery - Boston

City Winery - Boston

CHRISTMAS CALENDAR
The Rock Orchestra By Candlelight at Wang Theatre
Tue, 16 Dec at 08:00 pm The Rock Orchestra By Candlelight at Wang Theatre

Wang Theatre

ART THEATRE
Parking Harry Potter and the Cursed Child - Boston
Wed, 17 Dec at 12:00 am Parking Harry Potter and the Cursed Child - Boston

Emerson Colonial Theatre

ART THEATRE
Parking Utah Mammoth at Boston Bruins
Wed, 17 Dec at 12:00 am Parking Utah Mammoth at Boston Bruins

TD Garden

TRIPS-ADVENTURES
Utah Mammoth at Boston Bruins
Wed, 17 Dec at 12:00 am Utah Mammoth at Boston Bruins

TD Garden

CONTESTS TRIPS-ADVENTURES
Boston Ballet: The Nutcracker
Wed, 17 Dec at 12:30 am Boston Ballet: The Nutcracker

Citizens Bank Opera House

TRIPS-ADVENTURES
Board Game Speed Dating for Gay Men at Club Caf\u00e9
Mon, 27 Jan at 07:00 pm Board Game Speed Dating for Gay Men at Club Café

Club Café, Columbus Avenue, Boston, MA, USA

WORKSHOPS
Board Game Speed Dating for Queer Women at Club Caf\u00e9
Mon, 24 Feb at 07:00 pm Board Game Speed Dating for Queer Women at Club Café

Club Café, Columbus Avenue, Boston, MA, USA

SPEED-DATING WORKSHOPS
Boston Blind Date Matchmaking and Membership
Thu, 13 Nov at 07:30 pm Boston Blind Date Matchmaking and Membership

Boston

SPEED-DATING MEETUPS
Boston M**der Mystery: A Deadly Dating Game!
Fri, 14 Nov at 11:00 am Boston M**der Mystery: A Deadly Dating Game!

The George Robert Fountain

TRIPS-ADVENTURES CONTESTS
Advice Simplified | Relationship Coaching by MyCheekyDate
Sat, 22 Nov at 10:00 pm Advice Simplified | Relationship Coaching by MyCheekyDate

Boston

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

Boston

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

Boston

SPEED-DATING
*FLASH SALE 35%* As Seen on VH1 | Blind Date Matchmaking in Boston
Thu, 11 Dec at 12:00 am *FLASH SALE 35%* As Seen on VH1 | Blind Date Matchmaking in Boston

Boston

SPEED-DATING MEETUPS
30s Speed-Dating (Monogamous)
Tue, 16 Dec at 07:00 pm 30s Speed-Dating (Monogamous)

The Kartal

SPEED-DATING WORKSHOPS
Sips & Sparks Speed Dating  Over Martinis for Singles 50+ (men's ticket)
Thu, 18 Dec at 07:00 pm Sips & Sparks Speed Dating Over Martinis for Singles 50+ (men's ticket)

Savvor Restaurant and Lounge

SPEED-DATING HOLIDAY
Boston Speed Networking | NetworkNite | Business Professionals Event
Fri, 19 Dec at 07:30 pm Boston Speed Networking | NetworkNite | Business Professionals Event

Scholars American Bistro and Cocktail Lounge

BUSINESS SPEED-DATING
\u26a1 SpeedBoston Dating | Saturday Night Ages 29\u201342 | Boston\u2019s Speed Dating
Sat, 20 Dec at 07:00 pm ⚡ SpeedBoston Dating | Saturday Night Ages 29–42 | Boston’s Speed Dating

Scholars American Bistro and Cocktail Lounge

SPEED-DATING BUSINESS

What's Happening Next in Boston?

Discover Boston Events