PERFORMANCE 

The Second City Swipes Right: An Incomplete Guide to The Ultimate Date Night Like Add to a List
The Second City, Chicago's oldest ongoing improv theater troupe (and original stomping grounds of greats like Chris Farley, John Candy, and Amy Poehler) will head to Portland with an evening of caliente comedy and naughty hilarity that your Tinder date will dig.
Newmark Theatre, South Park Blocks (Fri Feb 10)

Valentine: A Night of Circus, Music & Love Like Add to a List
No Valentine's Day is complete without artistic juggling, so head to this circus performance—complete with aerialists, acrobats, and a live band—for a topsy-turvy celebration of love.
Alberta Rose Theatre, Concordia (Feb 13-14) 

Burlynomicon February Like Add to a List
Love-weary souls should head to Coffin Club's hallowed halls, which will soon creak to life with a decadent sensual delight. For this passion-filled edition of Burlynomicon, attendees can dine on Valentine's Day treats and ghoulish libations while feasting their eyes on burlesque apparitions and Cupid-struck cabaret performers.
Coffin Club, Buckman (Tues Feb 14)

ValenTango 2023 Like Add to a List  
The "largest and longest-running tango festival in North America" celebrates its 23rd anniversary this year with a wide range of classes, milongas, mixers, DJs, and orchestras, plus an unmatched lovey-dovey atmosphere.
Doubletree Hotel, Lloyd District (Feb 15-20) 

MUSIC

Your Song: A Valentine’s Singalong Tribute to Elton John Like Add to a List
No need to be alone this Valentine's Day; fellow members of the Rocket Club are here to help you get through it with a singalong celebration featuring Sir Elton John’s hits about love and loss. You may also hear some tunes from his friends and frenemies, too (*cough* Madonna *cough*).
Polaris Hall, Humboldt (Fri Feb 10)

Portland Gay Men's Chorus Presents: "It's Complicated" Like Add to a List
In the wise words of Avril Lavigne, "why do you have to go and make things so complicated?" The Portland Gay Men's Chorus (one of the longest-running gay men's choruses in the country!) will explore the many complex moods of love with uplifting choral renditions of pop tunes (think: Whitney Houston, Gloria Gaynor, Cher, Dolly Parton, etc).
Alberta Abbey, King (Sat Feb 11)

Under The Covers: A Pre-Valentine's Affair Like Add to a List
This Valentine's weekend, get cozy with local sweethearts the Moody Dudes, Pulp Western, and Falcon Heart as they cover classic love songs by artists like Hall & Oates, Beyoncé, and Boyz II Men that highlight the ups and downs of romance. 
Doug Fir Lounge, Buckman (Sat Feb 11)

Portland Chamber Orchestra Presents: Love, Chocolate and The Brain Like Add to a List  
Looking for Valentine's Day plans that are out of the ordinary? OHSU neuroscientist Larry Sherman will be joined by the Portland Chamber Orchestra and vocalist Naomi LaViolette for a thought-provoking, educational, and humorous multimedia discussion/concert that explores love, music, chocolate, and how the brain experiences pleasure. 
Patricia Reser Center for the Arts, Beaverton (Tues Feb 14)

FILM

Queer Horror: Picnic at Hanging Rock Like Add to a List
Grab your rose water and your candelabras, girls, 'cause nothing says Valentine's Day like a clique of dreamy boarding schoolers gone missing in Victorian-era Australia. This screening of Peter Weir's wistful madhouse Picnic at Hanging Rock is sure to take your breath away. Screened as part of the Hollywood’s bimonthly Queer Horror program, premier drag clown Carla Rossi will return to host the date night, which will open with a pre-show eleganza by unannounced "PDX all-stars."
Hollywood Theatre, Hollywood District (Tues Feb 14)

FOOD & DRINK

Valentine's Day Murder Mystery Dinner Like Add to a List
This Valentine's Day, "murder is on the menu" at King Tide. Channel your inner Benoit Blanc and solve the mystery at hand while indulging in a seafood-packed dinner buffet from chef Alex Diestra and wines from Argyle.
King Tide Fish & Shell, RiverPlace (Feb 9 & 13)

Treat Yourself Sip & Shop Market Like Add to a List
Bundle up and mosey over to this free Valentine's Day-themed market, which will feature a bevy of local vendors, food, treats, massages, bottle service, photo ops, and other delights. You'll even get to spend some time petting adorable farm critters.
Triskelee Farm, West Linn (Sat Feb 11)

COMMUNITY

My Muddy Valentine 5k Obstacle Run Like Add to a List  
You know what's romantic? Obstacle courses. Think about it—you wobble haplessly through a 5K or 10K course and conquer a challenge with your sweetie, covered head-to-toe in mud. Once you're done, you pop in one of the Plumper Pumpkin Patch's hot showers and changing rooms to freshen up, then chow down on complimentary grub and gulp down a beer, exhausted but basking in post-workout endorphins. For those that see love as a challenge, maybe this is what Valentine's Day is all about.
Plumper Pumpkin Patch and Tree Farm, Rock Creek (Sat Feb 11)