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By: Rabbi Yossi Ives

The concept of a “coffee date” has become increasingly common in the dating world. This term does not necessarily refer to the beverage consumed but rather to the more casual, low-pressure nature of the meeting. Compared to a traditional date, it involves a more relaxed setting with fewer formalities. It is often proposed when one or both parties are hesitant about a full-length formal date but are still open to exploring potential compatibility.

At times, the idea of a “coffee date” offers an opportunity to see if something more might develop. But, it’s important to ensure that this casual approach does not lead to a lack of investment or intentionality in the dating process. Dating is inherently meaningful and requires effort. Renaming a shidduch date as a “coffee date” should not become an excuse to lower standards.

A date is one of the most significant and even sacred experiences a person can undertake. It requires courage to meet a stranger, share personal information, and make oneself vulnerable without knowing what the future holds. While some may find this process easier than others, it always deserves to be approached with sincerity and respect. We shouldn’t be looking for ways to lessen the importance of the occasion.

Labeling a meeting a “coffee date” shouldn’t be at the expense of the amount of effort in appearance, preparation, or engagement. Likewise, using the label to justify dismissing someone too quickly—e.g., “it was nothing much, just a coffee date”— diminishes the respect and thoughtfulness that should accompany the dating process.

Chazal teach that since Creation, Hashem has been occupied with arranging shidduchim. Going on a shidduch date entails direct involvement with Hashem, akin to the Kohen Gadol entering the Kodesh Hakadoshim on Yom Kippur. With this perspective, dating should be approached with reverence, sincerity, and a sense of purpose.

The key is to use the coffee date as a stepping stone rather than an endpoint—an opportunity to open doors rather than close them prematurely. For those who choose to begin with a coffee date, it is essential to strike a balance—keeping the atmosphere relaxed while still treating the process with the respect and full engagement it deserves. A coffee date should be a tool to ease into meaningful dating, not a shortcut to avoid commitment or effort.

To reach the author: Yossi@DateWell.org

To read the article online: https://datewell.org/acquaint/the-coffee-date-approach-when-it-helps-and-when-it-hurts/

Dear Toby,

I’ve been searching for my other half, but every guy I date has flaws I just can’t accept. Should I lower my expectations or wait for someone who truly meets my standards? I’ve been dating for over 10 years! Toby, What advice can you share with me?

Dear Rachel,

I feel your pain. I feel the weight of every disappointment, every moment of hope that crumbled, every time you whispered to yourself, Maybe this is the one"—only to realize, once again, that it wasn’t.

Ten years. A decade of searching, of giving, of believing, only to be left with empty hands and an aching heart.

I hear you. And I know how exhausting it is to keep hoping when every road seems to lead to heartbreak.

But Rachel, please listen to me; this truth could change everything for you:

Perfection does not exist.
I know that’s hard to hear. I know how much you’ve longed for someone who checks every box, who never makes you doubt, who fits seamlessly into your life like a missing puzzle piece. But love isn’t a puzzle. Love is messy. Love is raw. Love is flawed.

The truth? Real love isn’t about finding someone without flaws. It’s about finding someone whose flaws you can live with, love through, and embrace as part of the beautiful, imperfect journey you’ll walk together.

Let me share something deeply personal with you.

A Lesson From My Own Family
One of my 14 children was in a relationship, and it was going so well. It felt like destiny—until the imperfections surfaced. Suddenly, they were faced with the same heartbreaking question you’re asking:

Do I stay, or do I walk away?

That’s when I shared with them a tool I created and share with hundreds of singles, daily.

The “5 Majors”Methodology.

This method changed their life. And it will change yours.

The “5 Majors” Methodology, helps separate what truly matters—the absolute non-negotiables that define your core values—from what doesn’t—the human imperfections we all carry. The things we can learn to accept, to love, even to cherish.

For my child, this realization was liberating. It brought clarity where there had only been confusion. Suddenly, they saw their partner for who they truly were—not through the lens of unrealistic expectations, but through the lens of what truly mattered.

That single shift changed everything.
And Rachel, it can change everything for you, too.

What you need to understand, deeply and unshakably:

✔️ Perfection is a mirage. We are all flawed. And that’s exactly what makes love so powerful—because it means choosing someone, not in spite of their flaws, but because of them.

✔️ Imperfections are not barriers to love; they are the very fabric of it. They allow us to grow, to learn, to build something real and lasting—something that can withstand life’s storms.

✔️ You don’t have to settle. But you do need to understand what truly matters.

✔️ Embrace the flaws. Not as burdens, but as the foundation of something breathtakingly real.

Rachel, when you let go of the illusion of perfection and instead focus on what truly counts, you’ll open yourself up to a love that is deeper, stronger, and more profound than anything you’ve ever known.

The Bottom Line
So, I ask you this, Rachel—are you waiting for a love that doesn’t exist?

Are you searching for a fantasy while the kind of love that could change your life is passing you by?

Because out there, somewhere, is someone who is waiting for you. Not a perfect version of you, not a flawless, idealized image—but the real you. With your quirks, your fears, your beautiful, raw humanity.

Someone who will see you, truly see you, and love you—not in spite of everything you are, but because of it.

Rachel, open your heart. Let go of the illusion. Because when you do, something extraordinary will happen:

You won’t just find love. You’ll find home.

And when that moment comes—when you look into the eyes of someone who is imperfectly, beautifully, wonderfully yours—you will finally understand:

This is what I was searching for all along.

Rachel, if you need help identifying your 5 Majors, I am here.

With The “5 Majors” Methodology, I will help you gain the clarity and confidence to choose a partner who aligns with your deepest values.

Together, we will find the path to a love that is real, lasting, and exactly what you’ve been waiting for.

With all my heart,
Toby Lieder
Matchmaker & Dating Coach
Tobydatingcoach.com

Shidduch #441: Sholom Schonbuch & Baila Taubenfliegel

Shadchan Chani Raksin relates: "I was working with wit Bochur, and while searching came across her resume on ChabadMatch It seemed very suitable and what they were looking for. I suggested my idea to both sides, and BH they got engaged!"