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:
- Each week, I’ll present a true-to-life dating dilemma.
- You’ll vote on how you’d handle it.
- The following week, I’ll reveal the results, along with my professional insights.
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:
Meet Sarah. At work, with friends, or running a therapy session, she’s engaging, witty, and warm. But put her on a first date? She becomes painfully shy and quiet. The real Sarah – the one who can keep a whole Shabbos table laughing – gets buried under a mountain of nerves.
She’s been on five first dates in the past few months. Not one has led to a second date. The pattern is always the same: she gets nervous, gives short answers, laughs awkwardly at the wrong moments, and leaves the date knowing she didn’t show her true self at all.
What makes this particularly frustrating is that Sarah isn’t typically a shy person. She gives presentations at work with confidence. With her friends, she is the center of attention. She’s known for her quick wit and being easy to talk to. But something about those initial dates seems to short-circuit her usual personality.
She recently confided to a friend: “The worst part is knowing that I’m so much more than what they’re seeing. By the time I get home and replay the date in my head, I can think of a dozen things I could have said or asked. But in the moment? My mind just goes blank
The Question Keeping Sarah Up at Night:
Will she ever get past this, or is she doomed to perpetual first-date awkwardness?
What Should Sarah Do?
Here are four potential solutions:
A) A) The Total Reset: Take a complete break from dating for two months. Use this time to try improv comedy classes – not to become a comedian, but to practice thinking on her feet without overthinking. Return to dating with new confidence and skills.
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.
C) The Action Plan: No more hotel lobbies. Request only activity dates – bowling, mini-golf, paint nights, anything that gives her something to do and creates natural topics to discuss. The focus shifts from “performing” in conversation to sharing an experience.
D) The Professional Help: Work with a dating coach or therapist who specializes in social anxiety. Learn specific techniques for managing first-date nerves, practice through role-play, and develop strategies tailored to her personality and challenges.
Each of these approaches comes with its own implications:
- Option A might turn her into a master of witty comebacks… but two months is a lot of Shabbos meals fielding the “So, are you dating anyone?” question.
- Option B tests out the whole “honesty is the best policy” thing. It could be a great way to clear the air – or it could lead to both of them nervously discussing how nervous they are about discussing their nervousness.
- Option C swaps the tried-and-true hotel lobby date. Sure, those lobby couches are comfy, but maybe bowling or mini-golf will give her something to focus on besides overthinking her last three 0ne-word answers. However, there’s always the risk that dodging conversation over coffee just means overthinking her mini-golf game instead.
- Option D brings in the professionals because sometimes you need more help than your best friend’s “just be yourself!” advice. Though explaining to people why she’s suddenly “busy” every Tuesday at 7 PM might require its own strategy session.
What’s Your Advice for Sarah?
There’s no universally “right” answer here. This is exactly why I’m curious to hear from both singles and parents. Your unique perspectives and experiences could shed light on different angles of this situation that Sarah might not have considered.
