I’m pressing pause on the Dating Dilemmas series this week because I want to talk about something that I need to hear this week.
When I write articles or give speeches, I either pull ideas from my coaching files or write from the heart about something I may be struggling with.
This week, I needed a reminder not to lose hope.
This message was written for singles longingly waiting for their bashert and parents dreaming of the day they’ll walk their child to the chuppah. But it’s not just for them. It’s for anyone waiting for a yeshua because hope is universal.
Hope is one of those things we all know we’re supposed to have. It’s beautiful in theory. But in reality? It’s messy. It’s exhausting. Some days, it feels like trying to hold onto a balloon in a hurricane.
How long can you keep believing when nothing seems to change?
When another suggestion falls through.
When another yes turns into a no.
When another friend gets engaged, and you’re still waiting.
You tell yourself to stay hopeful. To trust the process. To believe your time will come.
But what happens when the waiting drags on, and that quiet voice of doubt starts whispering, Maybe it won’t?
Maybe you’ve wondered if you’re doing something wrong. Maybe you’ve questioned if Hashem has forgotten you. Maybe you’ve stopped davening with kavana because you’re scared to get your hopes up again.
I get it.
I want to share a powerful story about one of my clients – Rivky.
Rivky’s Story: The Two Letters
Rivky was 26, and after years of dating, she was done.
Done with the first dates that went nowhere. Done getting her hopes up, only to have them come crashing down. Done davening and feeling like her Tefillos were bouncing off the ceiling.
She fell into a deep depression and stopped hanging out with friends, began to neglect herself, and barely left the house. What was the point? She had done everything right—davened, worked on herself, gone out with every guy she was supposed to—but nothing.
So, she sat at home and cried.
One night, while cleaning out a drawer, she found an old envelope. She picked it up and saw her handwriting. She opened it. Inside was a letter.
Dear Future Me,
When you read this, you’ll be at your vort, surrounded by family and friends. I hope you’re glowing. I hope your chosson is everything you dreamed of. I hope you never forget how excited and grateful you feel at this moment.
She had written it at 19, back when she assumed marriage was just around the corner. Now, seven years later, she felt she had nothing left of that girl. The dream she had written about had turned into disappointment after disappointment. She wasn’t glowing. She wasn’t at a vort. She wasn’t even sure Hashem was listening.
That night, she sat down and wrote another letter.
Dear Hashem,
I don’t know if You hear me anymore. I don’t know if my Tefillos mean anything to You. I feel invisible. I did everything right—I davened, gave Tzedaka, and did my hishtadlus. And still, nothing. I feel like You’ve forgotten me.
She folded it up and angrily stuffed it in the back of the drawer. She couldn’t bear to throw it away, but she also couldn’t bear to look at it.
And then, a few weeks later, something happened.
Her good friend showed up at her door.
“Get dressed,” she said. “We’re going out.”
Rivky shook her head. “Not happening.”
Her friend wasn’t taking no for an answer. “We’re going to the Rosh Chodesh kumzitz. You need to come.”
Rivky rolled her eyes. A kumzitz? The last thing she wanted was to sit in a circle of inspired, glowing women, singing their hearts out, feeling close to Hashem while she felt… nothing.
But her friend wasn’t leaving without her.
So, she went. But her heart was closed. She sat in the room, arms folded, determined not to be inspired.
The women sang one song after another.
Min hameitzar karasi Kah…
Shifchi kamayim libeich…
Acheinu Kol Beis Yisroel…
Machnisei Rachamim…
She sat there, stone-faced, seething inside.
What does any of this mean for me? Why should I ask Hashem for anything when He clearly isn’t listening?
And then, the women started singing:
Kol Berama nishma, Rochel mevaka al baneha…
A voice is heard on high—Rochel weeping for her children.
And then…
Mama Rochel, cry for us again…
Rivky looked up.
She looked around the room.
And she saw that there wasn’t a dry eye in sight.
Every woman—married, single, older, younger—was crying. Pouring out their hearts.
And something inside her shifted.
She understood that Rachel Imeinu wasn’t just crying—she was also waiting.
She waited to marry Yaakov, only to see her sister take her place. She waited for children, watching others build families while she remained empty. She waited until her final moment, buried on the side of the road, far from the place she longed to be. And she is still waiting, yet she never gives up.
Her tears aren’t a sign of despair.
They are a sign of hope.
Hashem told her:
Minee koleich mibechi, v’einayich midimah…Rochel, you can stop crying now.
Not in an impatient way. Not as if to say, enough already!
But in the gentlest, most loving way.
I hear you.
Your tears matter.
Your efforts will be rewarded.
V’shavu banim ligvulam…Your children will come home.
Rivky sat there, letting the words sink in.
She had spent so long believing that her pain meant she was forgotten. That her waiting was proof that Hashem wasn’t listening.
But maybe—maybe—He had been listening all along.
That night, she went home, pulled out the letter she had written to Hashem, and added one more line:
I still don’t understand. But I know You’re listening.
And then she cried—not from anger, not from resentment, and not from that hollow, aching place of Why me? Why is this happening to me?
This time, her tears came from a different place. It came from a broken heart that is longing to connect with Hashem.
For the first time, she understood the difference between despair that shuts you off from connection and a broken heart that brings you closer.
It was the kind of brokenness that is reaching out, calling to Hashem, even without answers.
The Difference Between a Broken Heart and Despair
There is a difference between a broken heart (lev nishbar) and despair (atzvus).
Rebbe Nachman explains:
- A lev nishbar—a broken heart—is someone who is in pain but still turning toward Hashem. They are calling out, trying to connect. And Hashem comes close to such people. A person with a broken heart may have questions and may not understand, but they know Hashem only does what is best for us.
- Atzvus, despair, is when a person feels completely disconnected. It comes from anger, resentment, and feeling abandoned. When they cut Hashem out of your life.
The Kotzker Rebbe used to say: “Nothing in the world is as perfectly whole as a broken heart.”
Karov Hashem l’nishberei lev, v’es dak’ei ruach yoshia… Hashem is close to the brokenhearted and saves those crushed in spirit.
Hashem is ready to heal our broken hearts—but we have to take the first step and ask. Hope begins when we turn to Him, even in the depths of pain and doubt. When we reach out, He is already reaching back.
After the Tears: Choosing to Trust
After the tears have fallen and the brokenness settles in, we’re left with a choice: to stay in the pain or to take a step toward trust.
Trust doesn’t mean having all the answers. It means knowing that even in the waiting, even in the struggle, and even in those moments of deep uncertainty, Hashem is still with us.
How do we get there? What does trust look like practically? There are five steps to trust:
1. Trust in the Process
Your story is unfolding exactly as it should. Every yes, every no—it’s all leading somewhere. Hashem isn’t delaying you. He’s preparing you.
2. Trust in Yourself
You have everything you need inside you. You are not “too much” or “not enough.” The person meant for you is looking for you—not a version of you that’s filtered for approval.
3. Trust in Others
Yes, you may have been hurt. But there are still good people out there—people who care, who see you and want to help. Don’t let past disappointments make you forget that.
4. Trust in the Outcome
The ending is already written, and it is good. You are not missing your chance.
5. Trust in Hashem
The most important – You are not alone. Not for a single second. Every tear, every tefillah, every moment of frustration—Hashem sees it all. Hashem is guiding, carrying, and leading you exactly where you need to be.
Maybe hope isn’t about waking up every morning convinced that today will be the day everything falls into place.
Maybe hope is choosing to believe, even when it feels out of reach.
It’s trusting that, even before anything changes, your story is safe in Hashem’s hands.
And that is enough.
