Personals

ATTENTION GENTLEMEN: Seeking eligible bachelors who are interested in real relationships. I am a highly reputable matchmaker who privately represents stunning, smart, and accomplished women. Women pay our fees, so there is no charge for men. Complimentary inclusion in our database. Join now: Bonnie@bonniewinstonmatchmaker.com.

Our client (54) is a sophisticated, adventurous, and accomplished woman who is embracing an exciting new chapter in life. A former trial attorney who built her own arbitration and mediation practice, she recently launched a personal concierge business and is making more time for the things she loves—including travel, fitness, wine, culture, and trying new experiences. She enjoys everything from the symphony and community choir to Jazzercise, cooking classes, learning French, and exploring new places. She seeks a confident, self-made man who is financially stable, tall, fit, and comfortable in his own skin. He should be curious, spontaneous, culturally engaged, and genuinely excited to make the most of life, from international travel and adventures to great meals and a good glass of wine. A dog lover with a healthy, active lifestyle, he should have a life and interests of his own while being ready for a meaningful relationship and plenty of laughter. Respond confidentially to martina@threedayrule.com.

Our Bay Area Gem is a striking brunette, slender, and extraordinary in every way! Based in Mill Valley, California, she is open to meeting men in the Bay Area/Southern California and the East Coast. At 5'5" and very fit, she radiates great energy, charm, and intelligence. Her educational pedigree includes Smith College, Stanford, and The University of Chicago, and yet she is unpretentious, genuine, and fun! We are searching for gentlemen (65-77) who are meaningfully engaged in the world and confident in any setting. Our "Gem" enjoys sailing, skiing, languages, reading, travel, and politics. Her ideal match is a wise, creative thinker who shares many of her interests and has a deep sense of humanity. You both have/had great careers and value family time with children and friends. Respond with bio/photo to: sandy@therighttimeconsultants.com.

Blonde, beautiful, and charming just begins to describe our private client based in Manhattan with a wonderful second residence in Connecticut. Confident and upbeat, her homes are havens for entertaining her friends and family and celebrating occasions with style, grace, and class. An accomplished entrepreneur, she continues to enjoy her successful private practice in the financial world, being philanthropic, and a life long learner. As successful and happy as she is, she is now much more interested in finding a wonderful and accomplished gentleman with a big heart and a great sense of joie de vivre. Abstractly, he is a fit businessman/entrepreneur who is sincerely looking for a great partner to share his already wonderful life. The demographics for this search are 62–74, 5'9"+, East Coast, liberal or moderate, generous, loves travel and family. Reply in private: sandy@therighttimeconsultants.com.

Our client (36) is a charismatic, accomplished, and down-to-earth woman with deep roots in the Bay Area. Born and raised in Los Altos, she is a Stanford graduate and former professional soccer player who went on to earn her MBA from Columbia Business School and build a successful career in banking, entrepreneurship, and sports investing. Today, she runs her own firm, invests in sports ventures, and enjoys an active lifestyle filled with travel, great meals, meaningful work, family, and giving back. She seeks a smart, confident, ambitious, and athletic man in his 30s or 40s who is intellectually curious, health-conscious, loves to travel, wants children, and strives to be great at whatever he does. He should be charismatic, moderate and open-minded, and ultimately excited to make the Bay Area his home base while building a life filled with adventure, laughter, deep conversation, and mutual support. Respond confidentially to erica@threedayrule.com.

SINGLES: Three Day Rule Matchmaking is looking for accomplished, relationship-minded singles of all ages to join our exclusive network of screened m embers. Our free network is used by our matchmakers to introduce exceptional people to our clients, giving you the opportunity to meet someone you may not otherwise cross paths with. Join our network at https://www.threedayrule.com/pool/lisa or email Lisa directly at lisa@threedayrule.com.

This dynamic and feminine woman is a born and raised New Yorker. She helms a successful real estate development company. Gorgeous, she’s 5’4”, in terrific shape, pursuing skiing, yoga, biking, hiking, tennis, pickleball, and golf. Travel and adventure are in her nature. She loves live music, theatre, and many cultural opportunities. Well-educated, she also enjoys the Knicks, Rangers, the US Open, Burning Man, and Art Basel. A foodie, she entertains at home, from casual to formal. An empty nester, this is the perfect time to meet our incredible catch! Bonnie@bonniewinstonmatchmaker.com.

Our client (34) is a warm, accomplished, and family-oriented physician living in New York City. A devoted mother to two young sons, she enjoys an active lifestyle filled with running, Pilates, travel, and time with family. She is thoughtful, independent, and has built a successful life and career, but is looking for a true partner to share it with—someone kind, supportive, emotionally present, and excited to be an active part of family life. She seeks an established, health-conscious Jewish man in his 30s or 40s who wants children, values family, takes care of himself, and is ready to build a loving partnership. She appreciates confidence and chemistry over a particular “type,” and is looking for someone who is comfortable in his own skin and won't compete with her, but will genuinely be there for her. A strong connection to Jewish life and a pro-Israel perspective are important. Respond confidentially to erica@threedayrule.com.

Our client (62) is a smart, thoughtful, and warm woman living in San Francisco. A Dartmouth and Stanford Law graduate, she spent her career as an attorney in government and at leading technology companies before recently retiring. She enjoys an active, intellectually curious lifestyle filled with travel, reading, cooking, exercise, great food, good friends, and time with family. She is also deeply committed to her community, volunteering with an organization that helps seniors remain in their homes. She seeks a kind, emotionally intelligent, and financially secure man who is intellectually curious, passionate about something, family-oriented, health-conscious, and excited to get out and experience life together. She appreciates someone confident but not arrogant, comfortable with both conversation and quiet, and open to travel, spontaneity, and building a meaningful long-term partnership. Respond confidentially to deni@threedayrule.com.

Our fabulous client is a delightful physician (Yale BS/Stanford MD). Born and raised in Cambridge MA, lives in DC. Travels from DC to Boston and to SF/Bay Area, to see family and friends. Deeply passionate about her grown kids, healthcare, and giving back. Very active, she enjoys the outdoors including golf, beaches (especially Cape Cod and the islands), the arts, photography, and investing. Brings warmth and energy and is quick with a smile and shared laughter. Her match is a healthy physician, scientist, or expert in his field, 65-76, an optimist with a kind heart. Bio/photo: sandy@therighttimeconsultants.com.

DC-based stunner. Our slender, fit, attractive, Ivy-educated, and very private client, a "woman for all seasons," talented, charming, and accomplished enjoys a man with a brilliant and purposeful career. Her match is a confident, 5'8" and above, fit, attractive gentleman, 68-78, accomplished, kind, good values, love of adventure and travel, family-oriented, and genuine. Contact: sandy@therighttimeconsultants.com.

Watching the sunset while holding hands on a sailboat and sipping a dark and stormy. Nestled on a cozy couch in front of a warm fireplace in the winter. If this is your vision for healthy, warm, romantic relationship, I can introduce you to a special gentleman who is looking for a partner to share his life. He is a Harvard Business School grad, an avid sailor, photographer, father, friend. Active, fit, 5'10". If you live an active life, are located in Greater Boston, are in your 60s or 70s, and hope to find a mature, romantic relationship that celebrates you as a special person, this may be your opportunity. Bio and photo: sandy@therighttimeconsultants.com

Stunning, worldly, and charming, our private client (5'5"), is a semiretired foreign affairs professional, a former US ambassador, now based in Washington DC. Multilingual and amazingly well- traveled, she recently concluded a stint as visiting professor at one of the top Ivy universities. Last year as part of her position she curated and led an amazing trip abroad to Africa with and for her students. The trip was a huge success. Now in the fall/winter of 2026, the focus is on curated introductions to men who are deserving of her external and internal beauty. Her many interests extend beyond the academic to music, fine arts, literature, and dance. Her match is a confident, successful, kind gentleman (65 to mid-70s—open to all ethnicities), who also shares her passions and love of fascinating travel, international literature, politics and art. I recently had the privilege of having brunch with her at the Waldorf in DC, and she is as dazzling and fun in person as she is on paper! Bio and photo in confidence: sandy@therighttimeconsultants.com.or 212-627-0121.

Our client (74) is a warm, generous, and intellectually curious woman with a lifelong passion for the arts, culture, and ideas. A former professional cellist, she moved to Philadelphia in the 1980s to lead marketing for the Philadelphia Orchestra and has since worked with NPR, Congress, and Children’s Hospital of Philadelphia. Today, she shares her love of art as a guide at the Philadelphia Museum of Art and enjoys an active, engaged lifestyle filled with biking, fitness, lectures, concerts, cooking, and community events. She seeks a confident, independent, and well-educated man who is intellectually curious, financially stable, culturally sophisticated, and has interests and opinions of his own. She values empathy, integrity, generosity, and a lively mind, and hopes to find someone with whom she can share everyday life and build a committed partnership. Philadelphia is preferred, though she is open to New York or Washington, DC. Respond confidentially to tori@threedayrule.com.

Our charming, highly accomplished private client holds a top position as professor at a coveted Ivy university known for its excellence right here in the Northeast. Petite brunette with deep, dreamy brown eyes, she is athletic and fit, living her best healthy and active lifestyle. During the day she loves outdoor activities: swimming, biking, etc., and enjoys theater, concerts, and the arts all year round. She hopes to meet an equally fit, accomplished, eligible gentleman, intellectually curious, kind, and generous of heart and spirit. He should have an advanced and/or Ivy degree and a thriving career. Our client brings much to a new relationship: she has studied abroad, is Ivy educated, well-traveled, and is multilingual. Her strong match embraces similar values, ethics, and cares about his effect on others and the world. He is 48-58; a high achiever, but fun and not overly materialistic; warm and grounded. Contact privately: sandy@therighttimeconsultants.com.

Our client (57) is a successful, warm, and outgoing woman living in Wilmington, DE. A Global HR leader, she has built an impressive career while maintaining close relationships with her family and longtime friends. She enjoys an active lifestyle filled with travel, pickleball, boating, walking, reading, good wine and martinis, and discovering new experiences. She is ready to find a committed partner who shares her enthusiasm for life and wants to explore the world together. She seeks a kind, confident, and accomplished man who is healthy and active, college educated, financially established, social, and has a great sense of humor. He should be comfortable with himself, motivated, curious, and open to growing together. Philadelphia, South Jersey, and Delaware are preferred. Respond confidentially to lauren.daddis@threedayrule.com.

Our private client is considered one of the top international academic and public policy leaders in his field of expertise. Based on the West Coast and connected to a renowned university department, his work takes him all over the country and around the world. At 6'3", he is articulate, kind,handsome, and the proud and fully engaged father of two thriving adult children. Born and raised in Canada, he came to the United States to attend Harvard where he received his Ph.D. He enjoys a wide range of interests: music is his top interest, and he plays in orchestras and chamber music ensembles whenever he can. Our client practices meditation, has a love of the outdoors: hiking, cycling, skiing, ocean kayaking, and recently resumed studying French. He is seeking a loving, kind, attractive woman in her late 50s-60s who is as engaged in worthwhile endeavors as he and would be happy to spend time with him on West Coast as well as Canada and all over the world. Bio and photo: sandy@therighttimeconsultants.com. Please be concise. All confidential.