Mention matchmaking, and you might think of old-world traditions or romantic comedies gone sideways. But for Jaime Bernstein, matchmaking is modern, meaningful work—and it’s both a calling and a career. As a professional matchmaker with the national dating service Three Day Rule, Jaime blends intuition, strategy, and a healthy dose of humor to help singles find real, lasting connection.
Now based in Cincinnati—thanks to family roots, kids, and the city’s surprisingly vibrant dating scene—Jaime brings a uniquely Jewish perspective to her work. Whether she’s matching newly divorced Gen Xers, helping Jewish millennials navigate dating with tradition in mind, or just offering the gentle push toward a second date, Jaime sees herself as part dating coach, part confidante, part yenta (in the best possible way).
In this Q&A, Jaime opens up about how she got started, what Jewish clients are really looking for, and why your snack preferences might say more about your love life than you think.
Q: How did you first get into matchmaking? Was it a career you sought out, or did it find you?
A: I like to say I got into matchmaking because matchmaking got into me. It started naturally—matching friends in high school, then colleagues during summer jobs—and my passion and success have only grown since.
Q: Have you always been the one setting people up—even before this was your job? (i.e., were you “the friend who plays yenta”?)
A: Yes, I have been setting up friends, family, and colleagues since I was in high school.
Q: What brought you to Cincinnati? What’s it been like doing this work here?
A: My husband’s family is in Cincinnati, and most of my family is in Ohio. We have two young kids and wanted to be closer to family. We also love the vibrant Cincinnati community.
Q: What’s your approach when you meet a new client? Is it more intuitive or analytical? Relationship therapist or best friend?
A: When working with matchmaking clients, I believe it’s important to strike a balance between being a trusted friend and a knowledgeable dating expert. The goal of an initial client meeting is to understand them deeply—both their tangible qualities and intangible traits—in order to identify who would be a truly great match.
Q: What’s one piece of dating advice you wish more people took seriously?
A: I wish more daters would go on more second and third dates! People give up too quickly!
Q: How does your Jewish identity inform your approach to matchmaking? Do you find that it gives you a different lens than your colleagues might have?
A: My Jewish identity helps me appreciate the value of culture and tradition and how that can impact the longevity of a relationship.
Q: What are Jewish clients looking for that might differ from non-Jewish clients? Are there unique expectations, pressures, or dealbreakers?
A: Many Jewish clients are looking to find a partner to raise a Jewish family.
Q: Have you had any particularly memorable Jewish couples you’ve matched—or stories with a very Jewish twist?
A: One of my first successful couples that I matched in Washington, DC was a Jewish couple—they have now been married over 8 years and have 2 kids!
Q: Have you noticed any trends among younger Jewish daters—like a return to tradition, or the opposite?
A: One trend I’ve observed is that many Jewish singles are seeking partners who understand and appreciate their Jewish background. More recently, I’ve also noticed a growing number of Jewish singles expressing a desire to connect with others who actively support Israel.
Q: How do you handle parents who want you to set up their kids? Any funny or tricky moments there?
A: I’ve worked with parents who want to be involved in the matchmaking process, and I help them understand the importance of balancing their hopes for their child with the client’s own preferences and goals.
Generational Dating:
Q: Gen Z is all about sliding into DMs—what’s the best and worst way to make a first impression there?
A: Best impression: Write a short-n-sweet engaging message. Worst: Write “Hi” or send inappropriate pictures.
Q: For Gen Xers and Boomers dating after divorce, what unique challenges or joys do you see?
A:
Challenges:
- Emotional Baggage: Many carry the weight of past relationships—whether it’s hurt, mistrust, or simply the fear of repeating old patterns.
- Family Dynamics: Adult children, co-parenting responsibilities, or blended family concerns can complicate new relationships.
- Changing Dating Landscape: Technology has transformed dating. For those who haven’t dated in decades, navigating apps and virtual communication can feel overwhelming or inauthentic.
- Expectations: At this life stage, people often have clearer (and sometimes narrower) views of what they want, which can limit flexibility.
Joys:
- Clarity and Confidence: With life experience comes a stronger sense of self. Many Gen Xers and Boomers date with more intention and less pressure.
- Emotional Maturity: Emotional intelligence, empathy, and perspective are typically more developed, leading to deeper and more meaningful connections.
- Freedom to Redefine Love: This phase offers a chance to experience love with a new lens—whether that means companionship, adventure, or personal growth. Ultimately, while dating after divorce later in life can be daunting, it also opens the door to rediscovery, authenticity, and unexpected joy.
Jaime Bernstein brings warmth, wisdom, and a deep sense of purpose to her role. And for Cincinnati’s Jewish community—and really, anyone hoping to find a meaningful connection—there’s something pretty special about having a matchmaker in our own backyard.
