For a night of jazz and tasty food, head to Jimmy Mak's, the premiere jazz club in Portland, which has live performances almost every night. Make a reservation at the Barrel Room for their lively and often raucous dueling piano shows. If you and your partner are feeling nostalgic for the music you grew up with, Jones Bar is the place to be, where you can dance all night to hits from the '80s and '90s. Take in an indie flick with your date at the Living Room Theater, which features intimate, home-theater-style viewing rooms. It also offers gourmet food options and a full bar.

Take your date to Mississippi Pizza on Wednesday evenings for Quizzissippi trivia game night. Team up with another couple to compete and answer questions that range from pop culture to local Portland facts. For the ultimate gaming couple, head to Ground Kontrol Classic Arcade to play vintage arcade games that will take you back to your childhood. The arcade also includes pinball machines, a full-service bar and food menu, and has themed game night events throughout the week. See who's the bowling master between the two of you at Grand Central Lounge, Portland's premiere upscale bowling lounge, which features 12 bowling lanes and a full-service restaurant and sports bar.

If you and your date love nature and the great outdoors, plan a hiking or biking date at Mt. Tabor Park, an extinct cinder cone volcano in the middle of the city. The park has a series of walking and biking trails, each with a different level of difficulty for you and your date to choose from. A little northeast of Mt. Tabor, Rocky Butte Natural Area is another city park known for its challenging hills, as well as its breathtaking view of the city at the summit; plan to reach the top by sunset for an unforgettable romantic ambiance. Plan a kayaking date on the Willamette river. You can rent a kayak from one of the many riverside outdoor companies in Willamette Park.

Explore the places, culture and food that make Portland the one-of-a-kind city that it is. Spend a day in the eclectic Pearl District near downtown. Once a worn-down warehouse district, it's been transformed into an arts and culture hub packed with galleries, independent shops and performing art venues. Stroll through the various art galleries with your date, pick out vintage books for each other at Powell's City of Books, or check out one of Portland's many microbreweries in the area, such as Bridgeport Brewpub, where you can arrange a private tour of its on-site brewery. If you and your date are foodies, take the Forktown Food Tour, which takes you to some of Portland's most beloved restaurants, as well as hip newcomers on the food scene.