The Shidduch Power Struggle

Welcome back to our weekly Dating Dilemmas series! First off, a round of applause to all you brilliant “dating coaches” out there đŸ‘. 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 A: 11%
  • Option B: 50%
  • Option C: 25%
  • Option D: 13%

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 twists on how to approach the situation. Let me share a few of the comments:

“Hands down B) The Direct Approach: Start each date with honesty – ‘I should tell you that I get pretty nervous on first dates, so if I seem quiet at first, that’s why. I’m actually much more outgoing once I’m comfortable.’ This sets the expectation and often gets others to open up about their own nerves.”

“I totally believe in honesty, being real, and being open. I’ve tried it on dates, and it works wonders! I have told boys that I’m nervous…it breaks the ice and makes everyone feel better, and then he’ll know that he’s not seeing the whole you. Also, when boys have been honest with me, it makes me respect them, ’cause at the end of the day the most important thing in a marriage is open communication. That’s my 2 cents!”

“I would choose option B, but maybe with a twist. If she thinks it might be uncomfortable to bring it up on the date itself, maybe she can ask the shadchan to give the guy a head’s up before the date, so that way he knows and is more open to continuing with her.”

“I think option D can be a good idea, but in my opinion, option B is even a better choice—just they gotta know not to over talk about being nervous, which shouldn’t be too hard.”

“Option C could work too! Activities can almost be a distraction from worrying about what she’s saying and ease nerves. Option B can even be thrown in with a saying like, ‘I’m glad we decided to do an activity, first dates can be nerve-wracking for me.’ Excited to see the results!”

My Professional Advice:

I actually think all the options have merit, but A and B would be my top choices.

Option A suggests taking two months off, which might not be realistic or feasible for many, but the idea of doing something like an improv class is gold. Learning to think on your feet and getting comfortable in social settings can be a game-changer for overcoming shyness or social anxiety. I know it’s not such a popular idea in our community—but it should be. (Who would sign up if I started one? đŸ˜‰)

Option B is straightforward and an excellent approach. It always helps to be honest about your nerves. Most people find it refreshing, and it often opens the door for deeper, more authentic connections.

Now let’s dive into this week’s new scenario!

THE SITUATION:

Meet Baila. She’s just starting to date and is excited about this new stage of life. But there’s one problem: she and her parents are on completely different pages about how to navigate the shidduch process.

Baila prefers to keep things simple—check a few references, gather basic information, and trust her instincts. Her parents? Let’s just say if the FBI ever needed help running background checks, they’d be the first ones called.

She wants to take things slow, wait for suggestions from people who know her well, and ease into the process. Her parents, however, believe she should meet with every shadchan under the sun, attend every singles event within a 500-mile radius, and basically turn dating into a full-time job.

Caught between their enthusiasm and her own preferences, Baila is feeling stuck. She wants to feel in control of her own journey, but she also doesn’t want to hurt her parents or dismiss their advice entirely.

The Question Keeping Baila Up at Night:

How can she maintain her independence while still respecting her parents?

What Should Baila Do?

A) The Boundary Setter: Have an honest conversation with her parents, letting them know she appreciates their involvement but needs to set boundaries. She can tell them her preferences clearly—minimal checking, no professional shadchanim yet, and a slower pace—and ask them to support her in the way she needs.

B) The Diplomatic Approach: Agree to a compromise. She can meet with a few shadchanim and attend an occasional event, while they ease up on the intensive background checks and constant suggestions. A little give-and-take might help everyone feel heard and respected.

C) The Independent Operator: Take the reins entirely. Baila can express gratitude for her parents’ concern but politely explain that this is her journey, and she needs to navigate it in a way that feels authentic to her—even if that means handling suggestions and decisions on her own.

D) The Stand-In Solution: Baila suggests that since her parents are so eager, they should go all-in and handle everything—meet the shadchanim, attend the events, and even go on the dates as her representatives. After all, if they know her so well, they can probably make a great impression on her behalf!

Each of these approaches comes with its own implications:

Option A sets clear boundaries, but her parents might remind her that “parents know best” (and they’ll probably have a spreadsheet to prove it).

Option B offers a middle ground but risks Baila feeling like she’s still giving in too much.

Option C allows Baila to take full control, but the fallout could include some world-class guilt trips.

Option D flips the script—It’s the ultimate “be careful what you wish for” strategy—Baila’s parents might quickly realize that meeting shadchanim, attending events, and going on dates isn’t as glamorous as it sounds.

I’m excited to hear all the brilliant advice all you dating experts will have for this week’s dilemma!

Missed last week dating dilemma? Click here to read it.

Got your own dating dilemma? Reach out to me! I’ll do my best to guide you to clarity—and try not to take your parents’ side. 😉 If you’re the parent who needs guidance… I’m here for you too!

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