San Diego has a way of making romance feel… unforced.
Salt in the air.
Golden light that lingers.
A city that practically insists you slow down.
If you matched at one of our San Diego events and found yourself wondering where to go next… here’s a little Cheeky guidance.
Because second dates here deserve the coastline.
🌅 La Jolla at Golden Hour
Start with a stroll at La Jolla Cove—watch the waves, keep it simple, let the conversation do the work.
Then grab something sweet from Bobboi Natural Gelato or coffee from Blue Bottle Coffee (La Jolla).
If it’s going well?
Keep walking.
San Diego’s best dates often happen between destinations.
🍝 Little Italy, Candlelight & Pasta
If you want something romantic without trying too hard: Little Italy.
Dinner at Civico 1845 or Ironside Fish & Oyster, then a slow walk past the lights of Piazza della Famiglia.
Optional (but strongly encouraged): dessert from Extraordinary Desserts.
🌿 Balboa Park, Soft & Cinematic
For a second date that feels like a movie but costs almost nothing: Balboa Park.
Pick a path, wander the gardens, linger at the fountains.
If you want a quiet “wow” moment, pop into the Botanical Building area.
Then end with cocktails nearby at The Prado.
Low pressure. High charm.
🍸 North Park, A Little Playful
If your match has banter and momentum, go North Park.
Start with cocktails at Polite Provisions or something natural-wine-ish at Mabel’s Gone Fishing.
It’s lively without being chaotic—perfect for a date that might turn into a third.
🌆 Gaslamp, But Make It Intentional
Gaslamp can get loud — but the right plan makes it feel chic.
Dinner at Lionfish Modern Coastal Cuisine, then a rooftop moment at Altitude Sky Lounge (especially if you want skyline + a little glam).
Second dates don’t need to be wild.
They just need to feel chosen.
San Diego is easy to love.
And when two people choose each other here — with the ocean nearby and the city glowing softly around you — it feels simple in the best way.
We love watching matches turn into second dates.
San Diego does the rest.