Dating Coaching

We Are In Your Corner

Named one of America’s top ten Relationship Experts.

Peggy and Richard Wolman
Peggy and Richard Wolman
  • We motivate and inspire you to find, create and keep a mutually loving and lasting relationship.
  • We teach you specific strategies to produce results from your personal and professional network, and from your online presence.
  • We design a custom dating action plan to launch (or re-launch) you into the world of dating.
  • We empower you to become your own matchmaker, to learn how to meet wonderful singles and to attract and keep the right one for you.
  • We create effective online profiles and select the photos to make your profile stand out and be unique to attract the men you want to meet.
  • We advise you about the best ways to communicate with men or women you meet online and on dates.
  • We teach you how to prepare for first date success and how to handle difficult questions.
  • We give you the skills you need to date with confidence to make dates fun, positive and worthwhile.


When I first met Peggy I was drawn to her warm and optimistic personality. And then I met her husband Richard who is perceptive, thoughtful and quick with a joke.  Together they make the dream team and they’ve helped me navigate the tricky waters of dating.  They’ve helped me develop the language to describe my best self and, more importantly, they’ve helped me figure out how to ask the right questions to really get to know someone new. With their guidance I’ve been able to stop and think about who I want to be in a relationship and what I need to feel fulfilled.  I believe that they’ve helped me open my heart and realize that the right guy could be out there anywhere and I just need to be ready to meet him.

– Samantha, Age 36, Cambridge


Explore Our Relationship Coaching Services

"Peggy, having you as my dating coach was a life altering experience.
I can't thank you enough."

-Julie, 47

Ask Yourself

Whether you are new to dating or getting back into dating, consider whether these statements. If they resonate with you, then dating coaching is a perfect fit to help you find love.

I recognize I need to improve my dating skills so that I can get out there and start having fun dating quality men.
I’m not sure what to talk about and what not to talk about on a first date or what to say, if anything, about seeing each other again, whether I want to or not.
I want proven strategies for getting dates and the relationship I want, but not sure where to turn.
I am willing to invest emotion, time, energy and resources in my search for someone wonderful.
I am open to having a coach and mentor who will hold me accountable.
Online Dating

Online Dating

At Peggy Wolman Matchmaking we believe that meeting people online is an invaluable addition to your dating resources. Willy Sutton, the notorious bank robber said, “Why do I rob banks? That’s where the money is.” We say, “Why go online? Because that’s where the singles are.” With an online presence, your chances of meeting someone special are significantly increased.

Online meeting has many other advantages. You only have one chance to make a first impression. Your photo is a glimpse in the mirror that helps you become more realistic about who you are and what you have to offer another person. And your photo also gives you an instant snapshot that enables you to see yourself as others see you.

Many clients ask, “Why do I have to go online? I’ve tried it and it doesn’t work;” or I’m a high profile person and can’t take the chance that friends or students or colleagues will see me;” or “everyone lies and all I get are horrible dates.” Going online is an important psychological experience. It reminds us that each of us is only one person among the many who are also looking for love and hoping to meet someone. Going online helps clients become more realistic about their expectations and overcome the shyness of telling the world that they are “looking for someone who will make me happy.” To compete in the modern world of dating, meeting other singles online is an advantage you can’t afford to pass up.

Highlights of our Relationship Coaching Program

Personality InventoryLearn more about your personality style.
Love Matters HotlineOur monthly call-in for clients to share thoughts, feelings and dating experiences
Dating StrategiesWhere and how to find great singles in your city.
Image ConsultingLook and feel your personal best.
Online DatingCreating, editing, profiles & photos, email correspondences.
Dating TipsHow to get asked out on second dates.
InsightsWhy does he or she suddenly stop calling?
Mock DatesTricky questions to master.
The CommitmentWhy don’t your relationships translate to marriage?
Exit interviewsLearn about how to make a good first impression.