A Mother’s Conundrum

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 emotional cards close to their chest. Or maybe you’re that person who finds it tough to open up. Either way, it’s a relatable challenge many people face in relationships.

Here is how you voted:

Option A – Lead by example: 32%

Option B – Gently bring it up: 36%

Option C – Change the scene: 9%

Option D – Step back and reassess: 23%

It was eye-opening to see how many of you backed the gentle yet direct approach. And seems like not many of you thought a change of scenery would make much difference on it’s own. Lol! 🤷‍♂

Here are some of your comments:

I’m thinking option A is the way to go here, especially if you mix it with option C. Nothing breaks down walls like seeing someone else share first. If Faigy still keeps things bottled up, that might be Arye’s sign that she needs more time. Who knows—maybe she got burned before and is scared to put herself out there again. Since Arye’s pretty invested, giving her space to open up somewhere more laid-back could be exactly what they need.

Thank you so much for starting this dating dilemmas series; I find it so interesting to read and vote on.

For this week’s dilemma, I would go for option A. Actually, a combo of A and C would probably go over well. And if that doesn’t help, then probably it’s time to reassess. (I don’t like B because I feel like it would be way too awkward for the girl.)

I don’t have an opinion on this week’s dilemma, but…. I have a friend who was in this exact situation. She was very guarded and the boy she was dating felt like there was potential but he felt she wasn’t sharing enough to build an emotional connection. She decided to ask me my opinion and I was very honest with her and told her that I experienced the same dynamic in my relationship with her and I was secretly always worried how she would have an emotional connection with her husband. Once she heard it from me, she realized it must be true and that it’s something about her (even though it was hard for her to hear it!) The shadchan gave her a few tips and pointers and she practiced with me how to open up and share more…. and BH now they’re married!

“Here’s what I’m thinking: keep these options but shuffle them a bit. Start with A—share something real a few times. If that’s not getting anywhere after a few dates, try C. Give that a few shots, and if she’s still not letting those walls down, then it’s time for B—have that talk. If nothing changes after all that, maybe it’s time to face the music about whether this match has legs. Not saying this plan’s perfect, but it makes sense to me.”

My Professional Advice

I think mixing things up will work great here (and keep everyone’s dignity intact): Kick off with Options A and C together. Think about it—it’s way easier to get real when you’re doing something fun and low-key, like taking a walk or trying not to completely embarrass yourself at mini-golf. When the pressure’s off, Faigy might feel more comfortable opening up, and Arye can show her that being vulnerable isn’t the end of the world.

If that combo doesn’t do the trick, then yeah, it’s probably time for Option B—the honest chat. By this point, Arye’s already shown his cards, so he can keep it simple: “I really like spending time with you, and but I’d love to get to know you better. Is there anything I can do to help with that?” It’s direct but not dramatic.

And if nothing’s clicking after all that? That’s when Option D comes into play. Relationships are supposed to be a two-way street. If Faigy’s still got those emotional barriers up after all this effort, Arye needs to ask himself if he’s the only one trying here. Sometimes the answer’s yes—and that’s when you know it’s time to hit pause and think things through.

Now, what if you’re the one who finds it hard to let people in? Start small—nobody’s expecting your life story on the first date. Talk about something simple, like what’s on your mind today or that weird thing that happened at work. And if it feels awkward? Say so! Something like “Sorry, I’m not great at sharing stuff, but I’m working on it” can actually help break the ice. Remember, trust is like a Jenga tower—you build it up piece by piece, and that’s totally okay.

Ready to tackle this week’s Dating Dilemma:

The Situation

A Mother’s Conundrum

Mrs. Greenbaum is grappling with a challenge involving her 24-year-old daughter, Leah. Leah was suggested a “perfect” shidduch—Yossi, 27—who spent years learning full-time before transitioning to work. Yossi explains that his friends, who are already married, began working earlier than him. He stayed in Yeshiva much longer – but because he is still single, it is considered taboo to not remain in full-time learning. Now, he is kovea itim and still keeps Torah front and center in his life while starting his career so he can support himself and eventually a family.

The catch? Leah’s always dreamed of marrying someone who’ll dedicate those first 3-5 years to full-time learning. Even though Yossi checks pretty much every other box, Leah won’t even meet him, and Mrs. Greenbaum’s pulling her hair out thinking Leah might be passing up something great.

The Question Keeping Mrs. Greenbaum Up at Night:

How can I help my daughter see the full package and consider whether Yossi could be the right match for her?

What should Mrs. Greenbaum do?

Option A – Flip the Script

Get Leah to grab a pen and paper and write down what really matters to her in a husband—you know, the big stuff like kindness, shared values and life goals. Then, see how Yossi stacks up. Sometimes seeing it in black and white helps cut through the noise. “Hey, look at what you wrote—does this guy match what you’re actually looking for? Or are you stuck on how you thought things would play out?”

Option B – Leverage Peer Influence

Let’s be real—sometimes mom advice goes in one ear and out the other. But a friend? That’s different territory. Maybe Mrs. Greenbaum could get someone Leah trusts—a seminary roommate, friend, anyone she actually listens to—to casually mention that Yossi sounds worth checking out. It’s amazing how “Come on, what’s one date going to hurt?” hits different when it’s coming from a friend.

Option C – The One-Date Challenge

Make it feel like less of a big deal: “Just one date. That’s all I’m saying. If it’s terrible, you never have to see him again—and I’ll make your favorite dinners for a week.” Sometimes, taking the weight off makes it easier to say yes. Turn it into something light, maybe even fun, instead of this huge life decision.

Option D – Step Back and Trust Leah

It’s tough, but sometimes the best move is no move. Just tell Leah you trust her judgment, even if you’re biting your tongue. “Look, you’re smart, you know what you want, and I’ve got your back either way.” Giving her space might actually make her more willing to think it over, especially without feeling like mom’s watching her every move. Plus, it gives Mrs. Greenbaum a break from all the worrying – (as if that’s possible…)

Things to Consider before giving your feedback:

Option A – Flip the Script

This isn’t about crushing Leah’s dreams—it’s about helping her zoom out and see the bigger picture. Writing stuff down might seem old school, but sometimes seeing your thoughts on paper hits different. Just be ready for some resistance—nobody loves having their perspective challenged, but sometimes that’s exactly what we need.

Option B – Leverage Peer Influence

Real talk: moms can sometimes fade into white noise, but a friend’s opinion? That hits home. Getting someone Leah respects to casually mention Yossi could plant the seed. Just keep it low-key—the second it feels like a setup, game over. Pick the right friend and it could work magic; pick the wrong one and you might make things worse.

Option C – The One-Date Challenge

This is all about making it feel light and breezy. No pressure, just a “why not give it a shot?” kind of vibe. Maybe even make it fun—turn it into a little bet or challenge. But read the room—if Leah sees even one date as compromising her principles, this could backfire. It’s all about timing and keeping things playful.

Option D – Step Back and Trust Leah

This might be the toughest pill for Mrs. Greenbaum to swallow, but sometimes backing off speaks louder than any advice. Show Leah you trust her to figure this out. No pushing, no hints—just support. Sure, she might stick to her guns, but removing the pressure might be exactly what she needs to think clearly. Plus, it keeps the peace, which is worth its weight in gold.

I can’t wait to hear what wisdom you all have for Mrs. Greenbaum’s dilemma.

Want me to bring my relationship insights to your next event, workshop, or mixer?

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