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My Interview With a Professional Matchmaker and Book Review

Leora Hoffman is a woman I have known casually from the neighborhood, with whom I reconnected at a networking group not long ago. Like me, Leora was a practicing attorney-turned entrepreneur who pivoted into a totally different field. I also taught guitar to Leora’s son for several years.

Leora gave a talk to our networking group to discuss her services and revealed that she recently had had a memoir published called Catch Me a Catch: Chronicles of a Modern Day Matchmaker. I couldn’t wait to get my hands on a copy of the book as I adore memoirs and autobiographies.

I love to support other women entrepreneurs, and like me, Leora was doing something very unique; as a result, I asked Leora if I could interview her and publish a review of her book on my blog. She kindly agreed. The book review follows this interview.

Q: Whom do you primarily serve in your matchmaking business?

A: Professionals seeking long term relationships. I specialize in the 50+ demographic, although I have members who range in age from 30-94.

Q: What percentage of your clients in this demographic have never been married versus how many have been divorced or widowed?

A: Given that I specialize in an older demographic, the percentage of people who have never been married is much smaller than in the general singles’ population. In my membership, approximately 30% have never been married, while 70% are either divorced or widowed.

Q: Which of those groups are the hardest to match and why?

As common sense would dictate, those who have not been previously married are a bit more challenging. This is due to their entrenched single lifestyle, which can result in people’s inability to compromise, which is something that’s inherently ‘baked into’ people who have been married in the past.

Q: What type of services do you offer?

A: I offer 2 tracks of 'memberships.', as I call them. My 'active' membership, where I am actively working to match up the member consists of 3 levels of membership: basic, executive search and premium. Each level is priced based on the amount of time I invest over the membership period (12 months which can be spread over the 2-year window of time.) The Basic membership affords access to my entire network, and the Executive Search offers access to my network, along with recruitment beyond my membership from the community at large. I develop an ‘Action Plan’ that is unique to each client’s criteria, where I list the resources I plan to utilize to recruit prospects, which gives me a road map from which to work, and gives the client’s a sense of how I am investing my time on their behalf. This plan is updated every quarter.

The Premium membership is the Executive Search plus ancillary services which include: image consultation, photography, a personality profile (The Helen Fisher personality profile, which is similar to Myers Briggs, but is more applicable to one’s personal, rather than professional life), and a 3-hour relationship readiness class. The class follows a specific curriculum known as “Calling in the One”, developed by Katherine Woodward Thomas, where members are asked to visualize and articulate the attributes of the person they are seeking.

The most accessible type of membership track (not part of the three levels described above) is what I call my Resource Membership, which provides access to my database, so that members can be considered as potential referrals to appropriate active members. This involves a nominal, one-time registration fee which does never expires.

Q: Just to clarify, a Resource Membership entitles someone to be a part of your dating pool and be considered a potential match for one of your higher-level members but you will not actively search for a match for them?

A: Correct. Resource members serve as my pool from which I draw for my active clients for whom I am investing my time to find them matches.

Q: Are there other services that you provide if someone isn’t quite ready to become a member?

A: Yes. I also offer hourly 'relationship consultation services' which can be booked on an 'a la carte' basis for those seeking relationship advice, or online coaching support. I like to be flexible in providing services to benefit those with varying needs and budgets using my expertise.

Q: This is fantastic to know as people who have little experience in dating like I did before I met my husband could benefit from several coaching sessions with you. I really did not like dating as I found it very awkward. People who don’t necessarily need psychotherapy but could really benefit from a dating coach to help keep them on track would be well advised to seek out services such as the one you provide. I imagine you charge by the hour or offer packages?

A: Yes, I charge by the hour. If, at whatever point, the person decides to become an active member, I apply the fees that they have already invested in my services to their membership.

Renowned author and UVA professor of psychology Meg Jay, Ph. D. has said that finding a life partner is the most important decision one will ever make. It is unfathomable why one wouldn’t seek the advice of a professional. It should be a legal requirement before people are allowed to get married. That way, we wouldn’t have so many divorces! Most people seek professional advice on so many other important life decisions, but not the most important life decision! Why do you think there aren’t more matchmakers?

A: Matchmaking is a challenging profession. It requires excellent interpersonal skills, sensitivity, ability to advocate and persistence in the face of much frustration on client’s parts when things go south. As an incurable romantic, I am particularly suited to this work. When I started in this industry, there was almost no one doing this work. All you had were large corporate dating services, which in my experience, were not geared towards professional singles, or some well-meaning volunteers, usually the wives of clergy. Now that the stigma of working with a matchmaker seems to have lessened, the industry has exploded and there are many services across the spectrum with differing price points.

Q: Has Covid affected your business?

A: Actually, yes, for the better, oddly enough. It’s been well-publicized about how isolated and lonely people felt during Covid. As a result, people sought out my services to help them to connect to others; I set up Zoom meetings which creates a less intimidating environment than a face-to-face meeting in a traditional date.

Q: What is your background and how did you get into matchmaking?

A: I was a practicing attorney before starting my business in 1989. The idea was born when I was on maternity leave with my second child; I had a conversation with my sister in NY (where I grew up) about her having consulted a matchmaking service to find a partner. My instincts told me that such a service would be well-received in the DC, Maryland, Virginia Metropolitan area (“DMV”), to where I had moved in 1982. There really was very little in terms of matchmaking services in the DMV area.

Q: It must have been such a dramatic shift from the practice of law. How did you pivot to such an unrelated field?

A: I consulted an expert in helping people who wanted to create a start-up business; he developed a business plan for me, which I implemented over the next year. Ultimately, I left my legal position with a federal agency to start my company.

Q: How many years did you work both as an attorney and as a matchmaker before quitting your legal job?

A: Fifteen years.

Q: How has your practice changed over 33 years?

A: My practice always was, and continues to be small, personalized, and intimate. Despite the advent of the internet in the 90's, along with myriad of dating apps in the last ten years, I have stuck to the principles that made me successful back then and successful now. Getting to know my members on a deep personal level and communicating closely is key to my helping clients find the right person.

Q: It really distinguishes you from the pack -- impersonal dating apps that many find so off-putting, sterile and superficial, not to mention a bit scary! Who is your typical client?

A: My population is varied, but the common denominators tend to be the following: busy successful professionals with high standards who value vetted leads to attractive, high functioning, relationship-oriented prospects.

Q: What has your success rate been?

A: That would depend on how one defines 'success.' I can happily report that I am responsible for 82 marriages and hundreds of long-term relationships over the years. Success can also be measured by whether members go out a second time after an initial introduction. I would say that I am able to achieve that with approximately 50% of the referrals; it really varies depending on the level of membership of the parties involved, with a higher success rate amongst members for whom I've recruited prospects.

Q: What is your formula for a successful match?

A: Common goals, common values, strong physical chemistry, and a pinch of humor to help navigate the complexities of relationships.

Q: What is the biggest challenge for clients looking for love?

A: Insisting on everything on their 'wish list', not being open to new possibilities, wanting everything on their terms alone.

Q: How have your services helped people to overcome these challenges?

A: I have always preached pragmatism, flexibility, curiosity, and an adventurous spirit when it comes to dating. You cannot expect to hit it out of the park on the first go in finding your perfect match (although I have done so in rare cases over the years); but a suitable introduction to new people can educate and enrich people on their path to finding 'the one.'

Serving as an 'intermediary' for my clients, has given me the opportunity to put each referral in proper context and to field the feedback; this helps to protect against feelings of rejection with compassionate understanding and to encourage possibilities where they exist. Simply put, I am an advocate.

Q: These services really distinguish you from the impersonal abyss of dating apps – where there is no feedback and frequently, hurt feelings by one party. I hear a lot about the phenomenon of “ghosting” and have heard how painful that is.

A: Yes. I am a ‘buffer’ for my clients, protecting them from those experiences. If someone isn’t interested in the other person, I step in to gently and diplomatically inform the other party so that they aren’t waiting in vain to hear from the other person.

Q: Your book, Catch Me a Catch: Chronicles of a Modern Day Matchmaker is geared towards whom? (My review of this book follows this interview).

A: My book tells the story of my own search for love, going back in time and extending over the 30 plus years of my business, and how the two have intersected over the years. It applies to anyone who is interested in learning about matchmaking and relationships. For singles, it is a message of hope that love is possible at any stage. For those in relationships, it's a reminder that a good relationship takes work and effort to keep the spark and healthy communication alive.

Q: Sometimes, that includes getting some couples’ counseling, right?

A: Exactly.

Q: Do you think it’s a red flag if people do not want to pursue counseling, like somehow, they find it threatening?

A: Not everyone is psychologically minded enough to seek the support they need when differences arise in relationships. In the beginning, things should flow smoothly, but as relationships deepen, conflict is inevitable. If someone refuses to work with a partner who is interested in counseling to overcome those difficulties, that is indeed a red flag.

Q: What inspired you to write this book?

A: I was encouraged to write it by a good friend, who was a talented author himself, whom I met during my divorced years at a singles’ getaway. Over the years, I would recount my matchmaking stories, and he kept telling me that there was a book in there. I had never written a book, so I was reluctant to try. He died suddenly in 2017 and the shock of his death inspired me to organize my thoughts and begin an outline of what I had to say, as a tribute to him and our friendship. I was surprised at how easily the words flowed when I actually began. It turned out to be a very cathartic project for me personally, and a real love letter to my matchmaking clients over the years.

My Review of the Book:

I cannot tell you how much I loved Leora’s book except to say that I have read it twice and will probably read it again sometime in the future. I do not tend to re-read books unless I LOVE them. This is one of those books. This is partly because it is incredibly well-written in straightforward manner. Also, it is fascinating to read how a matchmaker can serve as an impartial third party to manage people’s expectations and are able to ground people in reality when it comes to finding a mate. As a former divorce attorney, it is my opinion that this lack of self-awareness and reflection is the cause of such a high rate of divorce in this country. Perhaps a matchmaker can help increase the likelihood of success of a marriage so it will not end in divorce.

Leora, twice divorced and currently married for a third time to a therapist, holds nothing back. She is candid to a fault about her relationship set-backs and shares the post-mortem of each one, forensically analyzing what went wrong in each situation. A fantastic lesson/gift that Leora imparts to the reader is the responsibility she takes for her own actions or failure to act and does not seek to blame the other party.

With the help of therapy over the years when needed, Leora generously shares insights she has learned in her own relationship troubles and the reader is privy to this invaluable information to apply to their own situation. Leora has faced a lot of adversity in her life, but never once does she wallow in self-pity. She is an incredibly strong woman; there is no BS about her, precisely what anyone would want in a matchmaker. However, Leora is polished, tactful, and compassionate in her frankness; you really feel as though Leora’s clients are very dear to her and she cares so much about their growth as they navigate finding a romantic relationship. Leora understands and respects boundaries and is sensitive to clients’ needs.

Leora’s vignettes of various client experiences provide a useful blueprint of what to do and what not to do in approaching various dating situations. What I have learned from the book is that being flexible and reasonable will go a long way toward establishing a healthy relationship. If one is intransigent in their beliefs and opinions, this will not serve one well if they are looking to form a serious relationship.

What I loved most about the book is Leora’s accounts of her personal life; these include not only stories of her various romantic endeavors but of growing up as a child of Holocaust survivors; she also shares a detailed account of why the marriage to the father of her children did not survive the challenge of her son’s autism. This was truly heartbreaking as Leora recognizes that her first husband is a wonderful father with incredible integrity and compassion, but who was not the right fit for her as a life partner.

Also incredibly riveting is Leora’s tale of her disastrous, albeit brief second marriage to an abusive man; in a weak moment, Leora married a man whom she realizes is not at all the person she thought he was. This horrifying epiphany comes within a day of getting married and Leora calls the Rabbi just moments too late to have the marriage annulled.

Finally, Leora’s long-term, long-distance, torrid romance with “Ian”, a British man living in outside of London is a gripping saga that is as emotional as any best-selling romance novel. Against all odds of the strength of their love and devotion, the heart-wrenching outcome of their relationship results in obstacles that are too large to overcome.

The book is beautifully written and flows so smoothly that it is an enjoyable and quick read. I really couldn’t put it down and made my husband listen to me read it aloud on a long drive. I can’t wait for Leora to put out another book. Bravo!!


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