Let’s face it, first dates can be awkward. But where you choose to go can make the difference between a great date or one that you’d rather forget. Here are some of our favorite first-date ideas at our restaurants, from Sangria Mondays at Lil-Ba-Ba-Reeba! to oyster Happy Hour at Quality Crab & Oyster Bah.


garnishing a piece of sushi - first date restaurants

Sushi-San recently launched a 45-minute/$45 omakase experience where talented sushi chefs create and serve 10 courses right in front of you. This is the perfect, low commitment way to get to know each other over pristine fish flown in from Tokyo daily. It’s kinda like speed dating, but with sushi! If your date is a dud, leave after the last course and you are out in less than an hour. If it’s a match, ask your server if you can move to a table to continue over an ice-cold Asahi or an order of Sushi-San’s fluffy Japanese Breakfast Pancakes with matcha butter.

Make a reservation for Sushi-San’s 45-minute omakase

Click here to learn more about Sushi-San’s 45-minute omakase


The Bamboo Room

The Bamboo Room bar for a First Date

The intimate bar (with low, mood-setting lighting) is a great spot to bond over a delicious tiki cocktail. Book a 90-minute guided tasting at The Bamboo Room and let the knowledgeable bartenders guide you through the world of high-end rums, complete with personalized crafted cocktails. This interactive experience (with a bartender buffer) is a sure way to keep the conversation – and drinks – flowing.

Make a reservation at The Bamboo Room

Here’s a look at a few of our favorite cocktails from The Bamboo Room’s new menu



Petterino's Monday Night Live for a first date

If you and your date prefer show tunes to sushi, check out Petterino’s “Monday Night Live.” Starting at 7:30 PM each Monday, this weekly impromptu musical showcase has dazzled for more than a decade with established and aspiring musical theater stars from Chicago’s stages to Broadway, cabaret artists, jazz, opera and more. Enjoy a drink and a bite before the curtain goes up and then sit back, relax, and enjoy the show (and the fact that you don’t have to continue to make small talk!)

Make a reservation at Petterino’s

Learn more about Petterino’s Monday Night Live here

Bar Ramone

Bar Ramone Tapas Bar

When you don’t know if you are doing just drinks or dinner too, stop by Bar Ramone for their complimentary, unlimited tapas bar during happy hour from 4:00 PM – 6:00 PM daily. No need to make decisions on what to order (except for which $7 wine by-the-glass you want), just grab a plate and fill it with whatever strikes your fancy. If the two of you are vibing, impress your date with your incredible porron skills and a couple more Spanish small plates. At least no one can say you’re boring!

Make a reservation at Bar Ramone

Learn more about the Spanish-style porron and how to use it


Tokio Asian Fusion

For a stellar first date in the Chicago suburbs, check out Tokio Asian Fusion in Schaumburg. Arrive between 4:00 PM and 6:00 PM and enjoy half-priced drink and food specials including potstickers, various maki rolls and spicy togarashi tots with Sriracha ketchup. If things are going well, stick around and share an order of Pork Belly Steam Buns or the signature Japanese Hot Rock Appetizer and take turns grilling slices of filet mignon or ahi tuna right at your table.

Make a reservation at Tokio Asian Fusion

Here’s a guide to date night at Tokio Asian Fusion from our friend, photographer Kailley Lindman


Stella Barra Pizzeria & Wine Bar

We know you’ll fall in love with the revamped Stella Barra Pizzeria & Wine Bar in Santa Monica, Hollywood, North Bethesda and Chicago’s Lincoln Park neighborhood. Grab a seat at the bar for a glass (or porron) paired with artisan pizzas, pastas and antipasti. Even if you don’t find your new favorite person, you’ll be sure to find your new favorite Italian wine!

Make a reservation at Stella Barra Pizzeria & Wine Bar – Santa Monica

Make a reservation at Stella Barra Pizzeria & Wine Bar – Hollywood

Make a reservation at Stella Barra Pizzeria & Wine Bar – North Bethesda

Make a reservation at Stella Barra Pizzeria & Wine Bar – Chicago


Joe’s Seafood, Prime Steak & Stone Crab

Joe's Seafood Oysters

Impress your date with a meal at Joe’s Seafood, Prime Steak & Stone Crab in Chicago, Las Vegas and Washington D.C. Rub elbows with the city’s power players over plates of stone crab claws and fresh oysters in the bar, or opt for dinner in the dining room and nosh on bone-in filet mignon or Dover sole with brown butter. Either way, make sure to add a slice of Joe’s signature pies for dessert.

Make a reservation at Joe’s Seafood, Prime Steak & Stone Crab – Washington D.C.

Make a reservation at Joe’s Seafood, Prime Steak & Stone Crab – Chicago

Make a reservation at Joe’s Seafood, Prime Steak & Stone Crab – Las Vegas


El Segundo Sol

El Segundo Sol Date Night Margarita

For prime patio seating and people-watching, head to El Segundo Sol on the Las Vegas Strip. During their daily Loco Hour, enjoy $4 draft beers and $5.50 regular or frozen margaritas alongside $3 tacos and $5 nachos. And if things don’t work out with this date, it’s ok. You’re in Vegas!

Make a reservation at El Segundo Sol

Our guide to where to happy hour in Las Vegas

For more date-night inspiration, check out these dishes and drinks perfect for sharing.