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Finding Forever Love

An Expert Matchmaker Tells the Inside Story to Finding a Successful and Lasting Relationship

Article by Erika Kaplan, VP of Membership

Photography by Courtesy of Three Day Rule

Originally published in Media City Lifestyle

What have you seen makes a good match?

A good match is less about checking off the typical boxes—like having the same hobbies or being physically attracted to each other—and more about deeper compatibility. It’s about how well your goals, values, lifestyle, and readiness for commitment align. Shared interests can make things easier, but they’re not the foundation of a lasting relationship.

At the core, a great match comes down to how you connect on a deeper level—how you both navigate life together and share similar values. If one person prioritizes career and independence while the other dreams of a family-focused life, those differences might eventually create tension. The same goes for mismatched expectations around communication or emotional availability. When values and priorities don't align, dissatisfaction can quickly follow.

One of the most important signs of a good match is a genuine curiosity about each other’s lives. You don’t need to share all the same interests, but being truly interested in each other’s experiences, passions, and goals helps build a strong connection. This curiosity shows that you respect each other’s individuality and are invested in each other’s growth. It’s this openness that helps a relationship stay strong through the inevitable challenges life brings.

Where is a good place to begin in thinking about what you are looking for in a partner?

The process of figuring out what’s truly important for a fulfilling relationship can take time, but it’s essential for clarity. A good place to begin is by making a list of priorities:

  1. Must-Haves: These are the non-negotiables—the qualities you absolutely need in a partner for the relationship to work. They might be emotional maturity, shared life goals, or perhaps certain values, like honesty or kindness. Be specific about what you cannot compromise on.
  2. Nice-to-Haves: These are the traits or qualities that would enhance a relationship, but aren’t dealbreakers. For example, you might want someone who enjoys hiking or traveling, but you could still be open to dating someone who doesn’t share this interest as long as they are supportive and understanding of it.
  3. Dealbreakers: These are the things that, if present, would make a relationship impossible for you. For instance, if you want children and your partner doesn’t, that’s a dealbreaker. Or if you have strong religious beliefs that are important to you, it’s vital to find someone who shares those or respects them deeply.

We recommend narrowing this list down to three must-haves, around ten nice-to-haves, and up to three dealbreakers. This process helps keep expectations grounded and ensures you're not trying to fit a "perfect" person into a box, because, honestly, in all the time I’ve done this I’ve learned that perfection doesn’t exist. Instead, the goal is to find someone who aligns with your most essential needs and values, while remaining open to differences that can enrich the relationship.

What are some first date ideas?

A first date is your chance to spark a connection—not necessarily to reveal your entire life story, but to provide just enough about yourself to leave the other person curious for more. The primary goal is to get a second date. It’s about offering a snapshot of who you are without overwhelming the other person with too much too soon.

For a first date, it’s important to choose a setting that encourages conversation. You want a relaxed environment where you can actually talk and get to know each other, so opt for places like a coffee shop, a cute bar, or a quiet café. A walk in a park or in town can also be a great option—something that combines the chance for conversation with a bit of movement to keep things comfortable.

First dates shouldn’t be about impressing each other with extravagant gestures or trying to sell an idealized version of yourself. Instead, they should be a chance to gauge if you feel comfortable together and if there's a natural flow in conversation.

What kinds of questions do you ask a person on a first or second date?

When it comes to asking questions on a first or second date, the goal is to create an atmosphere of openness and curiosity without making the other person feel like they’re being grilled. Open-ended questions are a great way to start, as they give both of you the opportunity to share more about yourselves. Avoid questions that can be answered with a simple "yes" or "no"—they tend to shut down the conversation.

For example, ask things like:

  • "How do you usually spend your weekends?"
  • "What’s something that’s on your bucket list?"
  • "What’s one thing you’ve learned this year?

The key is to stay genuinely curious. The best way to create a connection is by showing a real interest in their thoughts and experiences. Your questions should allow the conversation to flow naturally, and you should be prepared to share your own thoughts and experiences as well.

What are some things a person should pay attention to when dating?

It’s important to stay aware of a few key things that can really impact whether a connection will last in the long run. Things like:

  1. Goals and Intentions: When someone tells you what they want out of life, believe them. If they say they’re not interested in something serious or don’t see themselves having kids, don’t expect that to change over time. People’s core goals and intentions typically stay consistent, so it’s important to listen closely to what they’re saying about the future. If you’re looking for different things, it’s better to recognize that early on.
  2. Communication Style: How do you communicate with each other? Healthy communication is essential to any strong relationship. Are you both able to share your thoughts openly and feel heard, or do you find yourself shutting down or not feeling understood? It's worth paying attention to how you both express yourselves.
  3. Respect for Boundaries: Early on, notice how well your boundaries are respected—whether they’re emotional, physical, or about your time. Are they considerate of your space and needs? Or do they push for more than you’re comfortable with? Feeling safe and respected is a key part of any healthy relationship.
  4. Energy and Effort: Relationships take effort from both sides. Pay attention to how much energy you’re both putting into staying connected—whether that’s planning dates, keeping in touch, or learning about each other. Is there a shared sense of excitement and commitment, or does it feel one-sided?
  5. Priorities: Take note of where this person is spending their time and effort. Are they prioritizing work, friends, or other activities over making time for you? Do you feel like you’re being made a priority in their life, or does it seem like you’re always on the backburner? How someone allocates their time can give you insight into what’s truly important to them.

At the end of the day, dating is about discovering not just if someone else is a good match for you, but also what you really want in a partner and how you want to be treated. By staying open, curious, and mindful, you’ll be more likely to find a relationship that aligns with your values and goals.

About Three Day Rule:

Three Day Rule is a modern matchmaking service for high-intent singles seeking meaningful connections. Their unique "Three Day Rule" approach to successful dating guides singles through an intentional dating journey before, during and after a date. With a team of experienced Matchmakers and a proven track record, they focus on relationship wellness and long-term compatibility, helping clients build authentic, lasting connections. Dating is more than just meeting someone—it’s about building a connection that lasts. Three Day Rule helps you take the right steps toward finding a healthy relationship.

Apps make it way too easy to swipe past your soulmate. Signs of a good match is a genuine curiosity. It shows that you respect each other’s individuality which helps a relationship stay strong through the challenges life brings.  

Key things that impact whether a connection will last - Goals and Intentions, Communication Style, Respect for Boundaries, Energy and Effort Sharing, and Priorities