Washington doesn’t rush connection.
It’s thoughtful.
Measured.
A city where conversation actually matters.
If you matched at one of our Washington DC events and found yourself wondering where to go next… here’s a little Cheeky guidance.
Because second dates here deserve substance.
🌅 Georgetown at Golden Hour
Start with a walk along the Georgetown Waterfront just before sunset.
Grab coffee from Blue Bottle or pastries from Baked & Wired, then stroll along the water as the light softens over the Potomac.
It’s relaxed.
Charming.
The kind of setting where conversation deepens naturally.
🍷 Dupont Circle, Effortlessly Cultured
If the mood feels promising, head to Dupont Circle.
Dinner at Iron Gate or Floriana, followed by wine at Barcelona Wine Bar.
It’s intimate without being intense.
Elegant without being showy.
Very DC.
🌿 Capitol Hill, Understated & Warm
If you’re leaning cozy, wander through Eastern Market, then settle into dinner at Rose’s Luxury or something easy at The Duck & The Peach.
Capitol Hill feels personal.
Almost neighborhood-like.
Second dates thrive in spaces that don’t feel performative.
🍸 U Street, A Little Energy
If the chemistry is undeniable, lean into it.
Cocktails at Service Bar or live jazz at Blues Alley bring just enough buzz.
It’s confident.
Playful.
A little electric.
🌸 A Monument Walk, Done Right
Yes — the monuments.
But not midday with tourists.
Go late evening.
Walk from the Lincoln Memorial toward the Reflecting Pool.
DC at night is quiet. Reflective. Almost cinematic.
It makes big cities feel small.
Washington is known for power.
But it’s also a city of connection — of long conversations, shared ideas, and quiet moments along the water.
And when two people choose each other here, it feels deliberate.
We love watching matches turn into second dates.
DC handles the rest.