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If you had to describe last week as a food, what would it be? A warm, comforting bowl of soup? A half-burnt piece of toast because things didn’t go as planned? A five-course meal because everything somehow aligned perfectly? For me, last week felt like a cup of coffee that I forgot about and had to reheat three times before finally giving up and drinking it lukewarm. (This happens daily to me, just FYI, but don’t tell anyone.) Forgetting about

Last week, we discussed how to share important info about yourself on dates meaningfully. But communication isn’t just about talking. You can be the best at expressing yourself, but if the other person isn’t really listening, it won’t matter. So, this week, I am flipping things around and talking about listening. There’s good listening, and then there’s… let’s just say not-such-good listening. And the way someone listens? It tells you a lot about how they’ll communicate in a relationship. Since

We’ve all heard the advice: Be vulnerable. Open up. Share more of yourself. Sounds great in theory, but what does that even mean? You can sit across from your date and start spilling your deepest fears and biggest dreams, or share about that time you were two and threw a tantrum in a grocery store because they ran out of your favorite ice cream. (For the record, understandable.) But will that actually create a connection? Not necessarily. I hear this from

Trust isn’t something you actively think about when it’s there—it just is. But the moment it’s missing, it becomes impossible to ignore. Suddenly, every conversation feels like a puzzle you’re trying to solve. You find yourself analyzing their tone, rereading texts, and wondering: Are they telling me the whole truth or just the version they want me to believe? A strong relationship needs more than chemistry and compatibility; it needs a solid foundation of trust. No matter how beautiful a

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

You know what’s funny about dating advice? Everyone’s got some to give, but when it comes to themselves, nobody’s got it figured out! Last week’s story about a mother, a daughter, and a not-quite-perfect-on-paper match got me thinking about all the times I’ve seen a ‘perfect shidduch’ turn out to be perfectly wrong, and ‘not quite right’ end up being exactly right. And judging by your responses to Mrs. Greenbaum’s dilemma, I’m not the only one who’s noticed this. So

Is it really Tuesday already? Boy time flies when you’re busy analyzing other people’s dating dilemmas. Whether you’re here because you enjoy dissecting other people’s relationship puzzles, or you’re just avoiding your to-do list, I’m glad I could be part of your entertainment (or education) for the day. Looks like Arye’s story struck a chord with you all—judging by the amount of votes and comments in my inbox! Maybe you’ve been there yourself, trying to date someone who keeps their

Welcome back to Dating Dilemmas. Thank you to all those who voted and shared your thoughts on last weeks scenario. It makes this series so much more fun and relatable. Your ideas keep things interesting, so keep them coming! (You can vote on this page or by joining my email list.) The results from last weeks dating dilemma are in, and here’s how the votes broke down: The clear front-runners were A and B, and for good reason. Here are some of

Welcome back to our weekly Dating Dilemmas series! First off, a round of applause to all you brilliant “dating coaches” out there 👏. You did a fantastic job analyzing last week’s scenario and sharing your insights. It’s always amazing to see such a variety of thoughtful responses! Here’s how the results broke down: Option B seemed to be the fan favorite—direct and honest communication for the win! But you all brought some great ideas to the table. I loved hearing your perspectives—especially the creative

Welcome to Dating Dilemmas! The weekly series where you get to be a dating coach for a day! This is your chance to weigh in on real-life dating scenarios from my coaching practice (details changed for privacy, of course). Here’s how it works: Whether you’re actively dating, married, or guiding your children through the shidduch process, your perspective is valuable. Let’s pool our collective wisdom and tackle these dilemmas together! Ready for our first dilemma? Let’s Dive In The Situation:

Some of you may not like what I am about to say, but it needs to be said. It’s often more challenging to offer honest guidance that someone truly needs than to simply say the things that will make you popular. But my ultimate goal always was and always will be – to help singles get to the chuppah. And sometimes, that means having the courage to speak uncomfortable truths. There’s been an interesting trend in how the community approaches

I was recently trying to set up a guy in his upper 20s. He was what many would call the whole package: successful, tall, very good-looking, from a great family. On paper, he had it all. But every time I suggested a girl, he turned her down. Each rejection came with a new reason or excuse. After a while, I found myself wondering: “Does he really want to get married?” It was a passing thought—one I didn’t dare voice aloud.

Imagine a dating world where singles embrace their flaws instead of hiding behind polished profiles. What if, instead of boasting about being “easygoing” or “adventurous,” you led with your quirks? “I’m a master procrastinator” or “I forget my passport half the time” could spark genuine connections. In a society obsessed with perfection, we risk losing authenticity. What if dating felt less like an audition and more like an honest conversation? Discover the revolutionary idea behind the Anti-Perfect dating profile and explore how embracing imperfections could transform your dating experience.

We all want it. If you are dating, this is what you dream about. If you are already married, this is what keeps you going. We will do anything (ok, almost anything) to get it. What am I referring to? The deep, powerful soul connection that some couples seem to have – the kind that keeps them laughing together, supporting one another, and growing closer every day. Have you ever sat in a café or restaurant, noticed a couple deep

“דְּאָגָה בְלֶב־אִישׁ יַשְׁחֶנָּה וְדָבָר טוֹב יְשַׂמְּחֶנָּה” “Anxiety in a person’s heart weighs it down, but a good word turns it to joy” – Proverbs 12:25 The power of a good word can change someone’s entire world – and nowhere is this more true than in the dating journey. Let’s paint a familiar scene. A parent sits at the kitchen table, watching their daughter push away another untouched cup of coffee after yet another disappointing date. A shadchan reads the gentle

It’s that time of year again—the season of gratitude. Everywhere you look, people are sharing their endless lists of blessings: their perfect families, their dream jobs, their cozy homes. Some people seem to have gratitude down to an art form: “So thankful for my incredible husband and the magical life we’ve built together!” And there you are, wondering if you’re supposed to be grateful for just surviving another day without completely falling apart. Gratitude? Seriously? Let’s get real. What if

Imagine a gifted woman in Elizabethan England, pouring her heart into plays but forced to hide behind the name of William Shakespeare. Today, we have the freedom to embrace our true selves, yet many still wear masks in dating, fearing rejection. But real connections are built on authenticity. When we show up as our genuine selves—flaws and all—we attract those who appreciate us for who we truly are. Discover how to shed the masks and cultivate lasting love that celebrates your individuality. Are you ready to let your true self shine?

Dating… You’d think it’s the only thing happening in your life, right? It’s all anyone seems to ask you about—”How’s dating going? Any new updates? Met anyone recently?” Meanwhile, you’re juggling a hundred other things because, let’s be honest, life is so much more than just dating, especially around Succos. This time of year, it feels like all the decisions are piling up at once, and not one of them involves “Have you met someone yet?” With Succos fast approaching,