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There’s a principle I’ve been thinking about a lot lately — one that applies to almost every part of life: career, friendships, marriage, dating, and mental health. But for this post, I’ll play the role of dating coach — as the midnight date debriefers seem to think I am — and focus on how this plays out in the world of dating. Dating is full of mixed messages. One minute it’s: “You’re enough. Just be yourself.” And the next it’s:

Last week, we started exploring some ideas from my book Finding Forever, and talked about the first step in dating: getting clear on why you want to get married and build a life with someone else. This week, I want to take it a step deeper. Because once you know why you want to build something, the next question becomes: Who’s actually doing the building? And by that, I don’t mean the person you’re dating. I mean you. Is the life you’re living

Before we talk about how to date, let’s talk about why. I was ready to start sharing sneak peeks from my upcoming book, Finding Forever: From First Date to Soulmates – starting with dating tips, such as understanding red flags, communication skills, and how to stop overthinking. But then I paused and asked myself:Before we talk about how to date… do you even know why you want to get married? I say that only half-joking. Because if we’re being real,

There’s this weird, quiet heaviness that creeps in sometime between the first “Where will you be for Pesach?” message and the moment you find yourself watching a stranger on Instagram scrub their fridge in slow motion. You can’t exactly name it—but you feel it. The ache of knowing that, once again, you’ll be showing up to Yom Tov alone. No one really talks about this part — what it’s like to watch everyone else rush around, lists in hand, arms full

You ever find yourself saying something you believe… but only halfway? Like, “Everything happens in the right time.” It’s the kind of thing we tell others—and even ourselves—when life throws a wrench in the plan. When a door closes. When the thing we were hoping for just… doesn’t happen. We say it to be comforting. Reassuring. And somewhere inside, we do believe it. Kind of. Maybe. Sort of. This past Sunday evening, there was supposed to be an event—an evening

A few weeks ago, I almost stopped writing my weekly blogs. Not because I was too busy. Not because I had nothing to say. (I always have what to say—even when I don’t. It’s a talent, really.) And not because no one is reading them. You are reading this, I think. It was more that I just wasn’t feeling it. I felt off. Drained. Stuck. I had the kind of feeling where everything felt a bit heavier than usual, and

It always amazes me how quickly we shift from Purim into Pesach mode. One moment, we’re delivering mishloach manos, caught up in the energy of the day, and the next, we’re making lists, planning menus, and diving into the cleaning that somehow always feels bigger than we remembered. But we all know that Purim isn’t just about the fun and the simcha—it’s a day when the gates of heaven are wide open. A day when tefillah carries a different weight.

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.