What We Hear

Questions Singles Ask Us:

Frequently Asked Questions

 “Now that you’ve heard my whole story, are you still hopeful for me?”

Yes, once we agree to work together it is because we believe that finding love will be part of your life story. We believe that our method is unique and nothing can replace our personal approach. Our husband and wife team, backed by a seasoned coach, a dynamic image consultant, a talented photographer, our sensitive Director of Client Services, all work together to form real relationships with our clients. We take the time to understand who you are so that we can help all of our clients put their best selves forward. We meet in person, by phone, email or Skype with all of our clients from New England, New York, and across the country.

“Can you help me talk through and visualize what love at this age and stage could look like?”

You may be looking for a first loving, lasting relationship but haven’t had much dating experience, or haven’t enjoyed dating. You may be returning to dating after divorce or loss of a loved one and recognize you need help to meet the kind of person you want to meet. Love at this stage of life is remarkably similar to other stages.  It is the feeling of being with someone special who loves you for who and what you are.


“Can you help me manage my expectations?”

For conscious and unconscious reasons most likely you are continuing to repeat the same behaviors and unrealistically expecting a different result. To help you find more useful and successful results, we don’t focus on why you may still be single. We help you focus on what you are going to do about it, and are there to assist you every step of the way.

You may be looking for a first loving, lasting relationship. You may be returning to dating after divorce or loss of a loved one and recognize you need help to meet the kind of men or women you want to meet. You realize that what you have been doing to find love has not been working. Maybe you don’t have the time or energy to keep searching for your special someone; or, perhaps fix-ups from friends are few and far between. It may be that meeting men/women through online dating sites has been difficult, or is too time-consuming and frustrating.

BUT, you still believe and expect, as we do, that there is someone wonderful out there for you. We just have to find him/her.


Are there strategies for me to attract and meet desirable and eligible men and women?”

Our services, whether for men or women, include relationship and dating coaching because many clients are rusty, timid, or under-confident. Dating and relationship coaching educates you to become your own matchmaker by learning how to leverage your own, well established and under-utilized networks and connections to meet the men or women who you want to date and with whom you want to share your life.

Dating and relationship coaching will help you meet and date successfullyWhether you are a young adult whose dating experiences have been limited, or negative, or you are new to dating after a divorce or having lost your spouse, you will quickly discover that the world of dating has evolved significantly and requires an informed, confident approach. We will explore with you, the potential roadblocks to finding, meeting and dating, and help you overcome them to make your dating and search for love successful.


Do you recommend online dating? I’m concerned about my privacy, truthfulness and safety?

The key to finding love is to cast as wide a net as possible.  It may not sound very romantic, but finding love is a numbers game and online dating increases your odds. Willie Sutton, the notorious bank robber was asked why he robs banks. His answer: “Because that’s where the money is.”

Well, online is where the men and women are. There are eighty-seven million singles in America and forty million of them have either been on online dating sites or are currently have an online presence. The good news for women is that 52.4% of online users are male, and 47.6% are female.

You are justified to be concerned about privacy, truthfulness and safety online. For our matchmaking clients who may also choose to include online dating, and for dating and relationship coaching clients – for whom we create an effective online profile, choose fabulous photos, vet for admirers, and assist with email communication –  we address these topics to teach you how to have a safe and successful online presence.


I have been online before and it didn’t work. Why try again?

Seldom, if ever, have we had a client who was able to write an effective profile alone or even with the help of friends. Writing about yourself is hard, and conferring with friends who care for you is rarely helpful. We are objective and know what it takes to write an inviting, accurate, succinct and effective profile. And, we insist on a terrific photo, arguably the most important component of your online presence.  The combination of a strong profile and a terrific photo makes being online fun and successful for our clients.  If your previous online experience failed, most likely you tried it alone and without expert guidance.


Do you find people for me to meet only from your own Rolodex and database?

The introductions we make may be members of Peggy Wolman Matchmaking or are recruited from our extensive personal and professional networks in New England, New York and nationwide. We also collaborate with local or nationally recognized matchmaking colleagues.  We never make an introduction for our clients with someone whom we have not met, either in person or through video-conferencing, to assure discreet and carefully chosen matches for our clients.


Do you specialize in any particular age group?

We work with serious minded singles dedicated to finding love.  Although our clients range in age from twenty-eight to ninety, our primary niche is with the Boomer demographic.  Our personal experience as a happily married couple can be reassuring to our younger clients as we explore the questions and challenges of committed relationships. Our work with older adult clients is guided by our understanding of how life experiences may have influenced their search for love. For younger and older adults, we focus on authenticity and the choice to show up and to be real.


What are your fees?

Our matchmaking and dating coaching programs are customized to meet your individual needs. Some clients require less service, others more.  At our initial interview when we get to know each other, we decide together whether we are a good fit to work together and appropriate fees for our services.


How is my privacy assured?

As a client or as a free member, your Peggy Wolman Matchmaking membership guarantees you one-hundred percent confidentiality. We know that privacy is paramount in a personal business, such as ours, and is particularly important to our clientele, many of whom are in the public eye. We are sensitive to how our clients are perceived by family members, friends, colleagues, or business associates. We never share information without your permission. Privacy and confidentiality are as important to us as they are to you.