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:
“Work on yourself. Grow. Heal. Do more.”
It can feel like you’re being told to relax and be confident while simultaneously improving everything about yourself. And if you’re already exhausted by the emotional rollercoaster of shidduchim, this contradiction only adds pressure.
Should you be proud of who you are, or quietly panic that you haven’t yet “figured everything out”?
The “When-Then” Trap
It’s no wonder so many singles find themselves stuck in what I call the “When-Then” trap:
- When I feel totally confident, then I’ll date again.
- When I stop overthinking, then I’ll finally be ready for something real.
- When I fix this part of myself, then I’ll be worth choosing.
But here’s the truth: that “then” rarely arrives. There’s always another layer to unpack, another thing to improve. The finish line keeps moving.
What if you didn’t have to choose?
What if you could say:
“I’m growing, AND I’m already enough.”
“I have work to do, AND I’m allowed to be seen.”
“I’m still figuring things out, AND I can still show up fully.”
That’s the Power of AND.
Why We Get Stuck
Most of us were raised with some version of the belief that self-improvement requires self-criticism. If we want to grow, we need to be hard on ourselves.
Push harder.
Do better.
But if you’ve ever tried to motivate yourself through guilt or shame, you probably know how that ends: not with growth, but with burnout.
You can’t shame yourself into becoming the kind of person you want to be.
You can’t pressure yourself into connection.
You can’t turn yourself into someone “more dateable” by rejecting who you are.
It’s like trying to grow a garden by yelling at the plants. The louder you shout, the more likely everything wilts. What plants — and people — need is consistent care. Sunlight. Water. Patience.
Sad Reality
A girl I once worked with — we’ll call her Tali — said something I still think about often:
“I know I have a lot to offer. But I also know there are things I’m still working through, so who would want me?”
How sad is that? That she genuinely believed no one would want to date her because she was still a work in progress. As if being human disqualifies you from connection.
Raise your hand — or the virtual equivalent — if you’re a finished product.
If you’ve completely worked through everything.
If there’s nothing left to grow, to process, to figure out.
Exactly.
We’re all still in process. Some people are just better at hiding it than others.
You don’t need to be perfect to be dateable. You need to be honest, self-aware, and willing to keep growing.
But not flawless.
Tali wasn’t stuck because she had problems. She was stuck because she thought she wasn’t allowed to have any. Once she let go of that belief, everything shifted, because for the first time, she stopped seeing desire for growth as something that disqualified her.
Dating isn’t a reward for having everything figured out.
It’s a space where two people can show up as they are, in process, and figure out if they can grow together.
That’s what the power of AND is really about.
Three Beliefs for the Power of AND
1. You have inherent worth.
You were created b’tzelem Elokim — in the image of Hashem — with value that doesn’t depend on your résumé, your confidence level, or how many yeses or nos you’ve received. You are already enough. Not “someday.” Not “once you improve.” Now.
2. Accept where you are.
Every journey starts with an honest map. You don’t need to love where you are, but you do need to see it clearly. Think about those “You Are Here” maps in a mall — it doesn’t matter how badly you want to be on the third floor if you’re standing on the ground level. You have to locate yourself first before you can figure out how to get anywhere else.
Real change doesn’t start with where you wish you were. It starts with where you actually are.
3. Challenge limiting beliefs.
Just because you’ve thought something for a long time doesn’t make it true. Especially the thoughts that whisper things like, “You’re not ready,” “You’re too much,” or “You’re always the one who gets left behind.” These beliefs might feel familiar — even logical — but that doesn’t mean they’re accurate.
Try asking yourself: “Is this thought helping me become who I want to be?”
And if not, try replacing it with:
“I’m still figuring things out — and that’s okay. I can move forward even from here.”
Put It Into Practice:
Before your next date — or even before you respond to a suggestion — take a moment. Remind yourself of these:
💬 I can be a work in progress AND still be ready to date.
💬 I can want growth AND still value who I am today.
💬 I can take small steps AND still move toward something meaningful.
💬 I can hope for connection AND stop trying to perform for it.
No one walks into a relationship with every question answered or every part of themselves fully settled. The strongest connections are built between two people who are honest about where they are — not where they pretend to be.
You don’t need to choose between embracing where you are and working toward where you want to be.
You’re allowed to do both.
Miriam
