Whether it’s your first date or your 100th, here’s our shortlist of where to go and what to do for a date night in Bend when you want to add a something extra into the evening.
I’m no expert at dating in Bend. I had my share of the good, the bad and the ugly dates before meeting my partner. My only advice is to skip the standard small talk over brewery pints and try out some of these fun options for date nights. You’ll have more fun and probably get better stories out of it, too.
Stand-up Comedy
On one of my first Tinder dates in Bend, the guy took me to see live comedy at what was then Summit Saloon. It was a great idea for a first date because we were able to laugh and there wasn’t too much time for awkward small talk. There’s a great scene of stand-up comedy in Bend (even without Summit, R.I.P). Bend Comedy hosts stand-up comedy nights around town each week. They usually take place at Seven Nightclub downtown. Grab drinks at a bar downtown first, then settle in to laugh.
Trivia
Bend has a ton of options for trivia nights at bars and breweries. Get a group of friends together to make a team, or try it out as a duo. You’ll probably learn something new and impress your date with your general knowledge sans Siri. Silver Moon Brewing, The Astro Lounge, Worthy Brewing and The Lot all have trivia each week.
Wine Tasting
Craft beer gets all the attention in Bend, but the town has its share of intimate wine bars where you can try out some nice pours in a quiet atmosphere without emptying your wallet. In the Old Mill District, try a flight of wines at Naked Winery or Va Piano Vineyards. Both have a small section for outdoor seating, so you can enjoy sipping wine al fresco. In downtown Bend, find a collection of international wines at The Good Drop Wine Shoppe. And in NorthWest Crossing, Portello has a great food menu with snacks to enjoy on while you share a sip.
Films
There’s a reason dinner and movie prevails as one of the timeless date options. It’s a nice mix of casual conversation and pressure free entertainment, plus a movie can offer a glimpse into your date’s personality and tastes. In Bend, Regal has the new releases, McMenamins has the cajun tots and comfortable couches, but Tin Pan Theatre, recently purchased by BendFilm, shows a rotating selection of indie films that you won’t see anywhere else in town. Impress your partner with your cultured side by grabbing tickets to see a new film at the independent theater tucked away in the alley.
Games
Downtown Bend also has some fun bars where you can play games and drink, which is always a good way to pass the time on a new date without having to make too much small talk. Duda’s Billiard Bar has a handful of tables where you can show off your pool skills, as well as darts upstairs. Around the corner, Vector Volcano has old-school video games, offering endless replay of the classics that claimed so many of our quarter dollars as kids. Vector also has one of the city’s best pinball machine assortments and a selection of local brews on tap, so you can bond over your nostalgic sides while you drink. Still got more game? Head over to J.C.’s and play a round of giant Jenga (watch your toes!) and then drift down to McMenamins for a game of shuffleboard.
Happy Hour
Of course, there is always the old standby: happy hour. Less of a commitment than dinner, but a bit more formal than a round of beers, happy hour is a classic first date for good reason. Plus, it’s a good way to try out some of downtown Bend’s best restaurants without breaking the bank. Share some drinks, share some bites, and when the check comes you can either keep the night going with one of the ideas above, or part ways and make it back home in time for your favorite shows (which is what you really want to be doing anyways, right?).
