Valentine’s Day Date Ideas from 5 Local Experts

Chefs, designers, tastemakers and more give us the skinny on V-Day in Rose City

By Karly Quadros and Shannon Daehnke

Maybe it’s all this unexpected February sunshine, or maybe it’s because we’ve all spent the better part of the past two years trapped mostly inside, but this year, we’re more ready than ever for Valentine’s Day.

Still, Valentine’s Day doesn’t have to been corny (stay back, cutesy cards!) or boring (on a Monday this year, arguably the least sexy day of the week). We reached out to five local experts for their suggestions on how to bring back a little romance into our human-contact-starved lives. From cooking classes to crafts to coastal excursions, there’s no shortage of options for even the biggest Valentine’s Day cynics.   

For the food lovers ... 

Grandmothers everywhere will tell you the way to someone’s heart is through their stomach, and that's true no matter your age. 

“So many things just come down to food for me,” says Meredith Mortensen, the culinary maven behind Cookshop, SE Clinton’s hub for cooking classes. Sharing quarters with leafy plant store Potted in Portland, Cookshop can feel more like cozying up in a friend’s living room than a professional kitchen space. 

“I was a pastry chef for a long time and worked in restaurants, so I personally hate going out for Valentine’s Day,” says Mortensen. Instead of relying on overloaded service workers by dining out at a fancy restaurant, couples can get up to their elbows in flour and eggs making handmade pasta and learn to pinch together plump Japanese dumplings. Afterward, participants can gather around a communal table and share the meal with wine or, for the more COVID conscious, take their food to go.  

Meanwhile, lovebirds can grab a last-minute, hand-pressed holiday card from neighboring card company Paper Epiphanies or share a bottle of natural wine at Bar Norman. 

And for couples who would prefer a more intimate night in, Mortensen also sells kits with supplies to make your own colorful, airy French macarons, while fellow Cookshop teacher Leta Merrill is selling Valentine’s Day–themed kits to make ultra-cute, heart-shaped ravioli (pictured above). 

For the DIY die-hards ... 

“A successful Valentine’s Day does not mean you have to spend a billion dollars,” says Eden Dawn, coauthor of the Portland Book of Dates (and Portland Monthly’s beloved former style editor). In lieu of overpriced, candlelit dinners in crowded restaurants, Dawn suggests thinking local by grabbing a bottle of nice local wine, cooking a dinner at home, and having a dance party right there in the living room. She suggests pinots from Abbey Creek Winery, Oregon’s first Black-owned winery, or rosés from Loop de Loop, based at the foot of Underwood Mountain in the Columbia River Gorge.  

For the more adventurous couple, a day trip out to the Pacific is the way to go, says Dawn. “The coast is going to be absolutely beautiful this weekend. I would recommend getting up early and staying the day. A good hiking spot is Oswald West by the Neah-kah-nie Mountain, or there’s Short Sands there where you can watch surfers.” The more restless couples can liven up a long walk on the beach by hunting for agates at Agate Beach or Fogarty Creek State Recreation Area. 

If you‘re single (or if intimate romantic outings aren’t your wheelhouse), Valentine’s Day is a great excuse to whip out your DIY skills. “I highly encourage an at-home craft night,” says Dawn. “One year when I was single, I got my friends together and we made and delivered Valentine's cards for everyone we knew.” Dawn recommends raiding Collage or Scrap for everything from construction paper and glitter to stickers and gel pens. 

Final PSAs from Dawn: “This is primarily for the heterosexual men. No one wants a bear or a heart-shaped necklace.” Also, ditch the roses for a more unconventional bouquet from local flower curators Solabee or Colibri, and you’re guaranteed to get a better response. 

For the Valentine’s Day curmudgeon ... 

Let’s face it, Valentine’s Day doesn’t always feel like a holiday for you if you don’t have lots of money to spend on oysters, Champagne, and fancy pasta dinners. But that doesn’t mean that you can’t find other ways of celebrating love and beauty this February 14, says Peter North, founder and designer at queer-focused, undergarment design house Lost Boy. 

“I don’t date people. But I find that I have so much love for my friends, and that love feels forever,” says North. As a designer who focuses on intentional, slow, and sustainable garments, North is prioritizing artistic creativity and simple pleasures this year. 

“So many things feel confined to how we meet people in conventional ways. Meeting each other in unconventional ways really helps us find love in each other though. I love the craft of Valentine’s Day. Leaning into your craft to meet people is so great. It contributes to the community,” says North. Whether you’re a dedicated artist or just like to work with your hands, Valentine’s Day is a perfect excuse to create something out of nothing. 

As for places to go out on February 14? “Powell’s or a library. It sounds crazy, but I think quiet space is romantic. It’s where thoughts happen. Quiet space is where creativity reveals itself,” says North.  

For a night in (the bedroom) ... 

“Expectations are generally a mood killer. They [might] create anxiety or goal-oriented connection, which is, in my opinion, kind of the opposite of romance,” says Amory Jane, general manager of SheBop, a women-owned sex toy boutique in Portland. “So, I think of [Valentine’s Day] as an opportunity to do something different and fun, as opposed to a night that needs to be perfect or romantic, you know, just kind of lowering the expectations all around.”  

Jane’s recipe for slowing things down and taking the pressure off this Valentine’s Day is simple: good food, karaoke, and, of course, sex toys.  

Valentine’s Day is a busy time of year at SheBop. Whether it be toys or a box of aphrodisiac chocolates from Portland Chocolate Laboratory, sex-positive shops like SheBop try to offer a unique Valentine’s experience and a chance to get to know yourself, and your partner, a bit better.  

“You can pick out some toys together and just kind of slow down for a night in. Maybe read some erotica, play some games, explore some new toys—either with yourself or with a partner,” says Jane. 

And if you’re not quite ready to the dive into the world of sex toys this Valentine’s Day, SheBop has tons of resources for beginners as well sex-positive educational workshops—check out the shop's blog. Or, you can always just check out Jane’s other rec, the Baby Ketten Klub, a beloved longtime KJ's bar on SE Powell.

“I always recommend karaoke to people who are big fans of doing something different. Do like a private-room karaoke situation—something for increasing novelty. And then go home and get it on,” says Jane. 

For the night owls ... 

“I love Valentine’s Day, I think you can really make it your own,” says Gina Altamura, talent buyer for the Holocene, a nightclub in Southeast Portland. “If you’re partnered, it’s a fun excuse to have a nice evening and be really present with your partner, and if you’re single, I think it can be a nice time to practice self-love.”  

Altamura emphasizes the importance of self-reflection on Valentine’s Day. In single years past, she spent the holiday practicing manifestation rituals and pampering herself. 

“I think it’s a powerful time. [It’s a time to] think about what you really want, and kind of magnetize some of the love that you want to bring into your life,” says Altamura.  

This year, the self-proclaimed romantic will be spending the weekend with her partner at Breitenbush Hot Springs. But, don’t worry, Altramura has left us with her ideal Valentine’s Day Eve date night: complete with three stops at her favorite local joints across Portland.   

Stop 1: Dinner at the “unpretentious, yet romantic” Dove Vivi. Altamura’s favorite date spot for years, Dove Vivi boasts cornmeal crust pizza and to-die-for chocolate chip cookies.  

Stop 2: Drinks at Bar Diane, a natural wine bar in Northwest. You’ll walk through an alley of twinkling lights and enjoy wines that are very “Valentine’s feeling.”  

Stop 3: Hit the Holocene for some wine-drunk dancing! The club will be open until 1 a.m. on Sunday for its Valentine’s Day dance party: ’99 to Ibiza, featuring local DJs, and the ever-romantic jams of late-’90s and early-2000s house music.

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