In the Words of MyCheekyDate New York
Let’s talk about the question New Yorkers pretend they’re too cool to ask —
When’s the “right time” to get it on?
Because in this city, the timing debate hits differently.
How soon is too soon?
How long is too long?
Should you wait three dates? Three months? Three subway delays?
Should you let your building’s astrology girl decide for you?
Should you wait until you’re both free on the same night… sometime in April 2031?
Welcome to intimacy — New York edition.
Messy, fast, slow, inconvenient, electric, and impossible to schedule like a Pilates class.
💬 The Honest Truth (Straight Up, NYC Style)
Here’s the thing:
There is no one-size-fits-all rule — not here, not anywhere.
And anyone who says,
“Wait until date five,”
clearly hasn’t tried coordinating two Manhattan schedules, a Brooklyn commute, and a Queens roommate who never leaves the apartment.
At MyCheekyDate NYC, we’ve seen everything:
People who hook up immediately… and end up with a mortgage and a Labradoodle.
People who wait months… and it still fizzles faster than a Midtown brunch mimosa.
There’s no data, no timeline, no algorithm — not even ChatGPT — that can tell you the “right” moment.
Because intimacy isn’t a strategy.
It’s a connection.
💛 The Real Answer (Even If It’s Annoyingly Simple)
It’s right
when it feels right.
When you trust them.
When you feel safe.
When the subway somehow showed up on time and the universe just feels aligned.
The moment you’re internally saying,
“Yes. This feels like us.”
New Yorkers love rules — lines, signs, systems —
but intimacy doesn’t care about checklists.
Forget the noise.
Forget the dating podcasts.
Forget your coworker who thinks she’s a guru because she once read half a book on attachment theory at a Williamsburg café.
This choice is yours.
Period.
🌹 No Shame, No Stigma (Especially Not Here)
In a city where:
People fall in love over dollar pizza
Dump each other over cold brew
Move in after two weeks because “the rent situation just makes sense”
…judging someone for timing is absurd.
Whether you become intimate on date one or date ten:
Both choices are valid. Both choices are adult. Both choices are yours.
And anyone who makes you feel small for choosing what feels right?
Congratulations —
you just saved yourself a six-month situationship with someone who wasn’t emotionally cleared for takeoff.
Connection is built on mutual respect, presence, and honesty —
not the imaginary rulebook of “proper timing.”
💖 What We Believe — MyCheekyDate NYC
After watching thousands of New Yorkers date each other —
some cautiously, some recklessly, all charmingly stressed —
one thing is clear:
What matters isn’t when intimacy happens.
It’s why it happens.
Did it come from trust?
From attraction?
From laughter that stretched across a cocktail table in the West Village?
From finally finding someone who doesn’t cancel because “work got crazy”?
That’s the real foundation.
Not timing.
Not rules.
Not the opinions of strangers on the internet.
Just two humans, in one wild city, choosing each other.