The best date nights are the ones where you stumble onto something unexpected and very Portland. This turned into a hidden Portland date night with a dessert vending machine and the most flavorful gin martini I’ve ever had. If you’re looking for something fun, easy, and unique, this is a good one.

We started with dinner at Matador

Our original plan was simple. Dinner at Matador on East Burnside, which is one of our go-to date night spots. If you can make it in time for happy hour, they have great deals on food and drinks. If not (and we didn’t this time), the food is still worth the price. Their classic and contemporary Mexican dishes are always full of flavor, and since they’re a tequila bar, you can try a flight or just order a really good margarita.

After dinner, we decided to walk across the street because I remembered Pix Patisserie being there. I hadn’t been in years, but I figured dessert sounded perfect.

Couple kissing, taken from below looking up

Except Pix Patisserie wasn’t the same…

When we got there, the entire setup was different. On Apple Maps it still says Pix Patisserie, but in person it’s now Pix-O-Matic. Instead of a full patisserie, there’s a Zoltar fortune teller and a bunch of vending machines filled with desserts and random little items. It sounds quirky, but the desserts are still just as good as they used to be. The machines are available 24 hours a day, except about 3 to 5 in the morning, and they’re under cover so rain isn’t an issue.

It felt like we had wandered into something fun without trying very hard.

Couple on date night holding hands while walking on the beach

Then we discovered the secret gin bar next door

Right next door, in the same building, is Can Bar. I didn’t even see it on Apple Maps, so it felt like we had stumbled on a little hidden Portland date night spot. They’re open Thursday through Saturday from 4 to 10 pm and they make their own gin.

The guy running it was friendly and really helpful. I know almost nothing about gin, and he still took the time to explain things and gave my husband and me a sample of their house-made sage gin called Gin Through The Sages. It was incredibly flavorful. We ended up ordering martinis with it, and they were honestly amazing. He mentioned a new gin coming out soon that people say is even better, so we already know we’re going back.

And if gin isn’t your thing, they also have wine and champagne. And charcuterie!

Lesbian couple dancing on the beach during a date night

Combine the two for a fun, easy date night

Pix-O-Matic and Can Bar are business partners, which means you can grab a dessert from the vending machine and bring it right into the bar to enjoy with your drink. They also have a patio if the weather is nice. It’s a relaxed setup and everything feels simple and low-key, which is exactly the kind of date night I love.

Engaged couple kissing with a rainbow behind them

The perfect ending to an unplanned Portland date night

I wasn’t asked to write any of this and I’m definitely not being paid for it. We just ended up having such a fun, unique night that I wanted to share it. Our plan was simply to grab dinner at Matador, walk across the street for dessert, and head home. Instead, we discovered Pix-O-Matic, found a hidden bar and tried house-made gin next door at Can Bar, and turned a regular evening into something memorable without even trying. It wasn’t what we planned, but it ended up being even better!

Need more date night ideas? I have another blog post with 10 Unique Portland Anniversary & Date Ideas For Staying in or Going Out.