Once upon a time, LA first dates were about timing.
Traffic timing.
Sunset timing.
And whether parking would ruin the mood before it even began.
At MyCheekyDate Los Angeles, we see first dates unfold every week —
and one thing is always true:
The right venue makes LA dating feel effortless.
The wrong one?
Too loud.
Too sceney.
Too “are we being watched right now?”
So if you’re wondering where to take someone on a first date in Los Angeles —
somewhere relaxed, human, and genuinely enjoyable —
here are Cheeky-approved spots, broken down by neighbourhood.
Because LA dating works best when it doesn’t try too hard.
🌿 Silver Lake: Creative, Calm, Comfortably Cool
Silver Lake is ideal for first dates that feel thoughtful without feeling serious.
Cheeky favourites:
Pine & Crane — casual, warm, and perfect for easy conversation
The Black Cat — cozy booths, relaxed energy, and classic LA charm
Cafe Stella — romantic without being precious, especially in the evening
Why it works:
Silver Lake invites you to be yourself. No performance required.
🍸 West Hollywood: Social, Stylish, Effortlessly Fun
West Hollywood is lively, but when done right, it’s excellent for first dates.
Great first-date picks:
Employees Only (LA) — intimate lighting, great cocktails, no shouting
Jones Hollywood — old-school booths and timeless date energy
La Boheme — perfect for drinks, conversation, and lingering just a bit longer
Why it works:
There’s energy in the air, but the right spots keep things grounded and warm.
🌊 Santa Monica: Light, Open, Naturally Romantic
If you want your date to feel relaxed from the start, Santa Monica does the work for you.
Cheeky-approved ideas:
Bodega Wine Bar — cozy, intimate, and ideal for conversation
Elephante (early evening) — sunset views without the late-night chaos
Chez Jay — classic, unpretentious, and quietly charming
Why it works:
Ocean air lowers defenses. Conversation flows more easily by the water.
🎨 Venice: Playful, Curious, Slightly Unexpected
Venice is best for dates that feel exploratory — not scripted.
First-date favourites:
The Rose Venice — coffee, wine, or cocktails in a relaxed setting
The Whaler — casual, open-air, and low-pressure
Townhouse Venice — intimate, welcoming, and great for conversation
Why it works:
Venice lets dates unfold organically — no rush, no rules.
🏙 Downtown LA: Intimate Corners in a Big City
DTLA shines when you choose spots that feel tucked away.
Cheeky picks:
The Varnish — speakeasy vibes, excellent drinks, perfect acoustics
Seven Grand — whiskey-forward, warm, and conversational
Perch (early evening) — skyline views before the late-night crowd arrives
Why it works:
There’s something special about finding quiet moments in a big city.
✨ A Cheeky LA First-Date Rule
Choose places where:
You can actually hear each other
Parking stress won’t derail the mood
Staying longer feels optional, not expected
First dates aren’t auditions.
They’re introductions.
And LA has plenty of rooms that know how to hold one well.
💛 Why We Love Hosting Dates in Los Angeles
LA daters are thoughtful.
Curious.
And often much more grounded than the stereotypes suggest.
That’s why we believe in real-world connection here —
warm venues, friendly hosts, and spaces that make dating feel human again.
Because when the room feels right,
everything else gets easier.
And that’s very LA. 💫