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When, Why, and How to Date This Valentine's Day: Date ideas for first-hangs, long-term relationships, just friends, and solo dates

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When, Why, and How to Date This Valentine's Day: Date ideas for first-hangs, long-term relationships, just friends, and solo dates
[Art by Joanna Moyer-Battick]

Valentine’s Day operates on a number of levels. Of course it’s a consumerist nightmare — it’s almost boring to point that out, but it’s no less true. But if you squint, the whole thing also makes some sense. As the seasons go, we’re concluding a cycle of months where couples batten down together (November), perform the holidays in a drunken, sugar-heavy blur (December), and then contract into woolly cocoons of ginger tea and novels (January).

February is different — there’s nothing there. It’s just more January. All it brings is a dull, throbbing boredom and a slight hint of coming thaw. Why is this happening? No one knows, but it may be a good time to check in with your partner. If you’re single/looking/non-monog or in anything other than a standard couple, you’re used to the heavy lifting that comes from in-person winter dating. Or maybe you’re happy alone! Regardless, we’ve got you covered for every way to approach the next few romantic weeks of V-Day and its aftermath (which is also, let’s be clear, just more January).




Arcadia, where you can order a beer and dive into some Fortnite. [Photo: Francis Flisiuk]

Drinks: Casual can mean a lot of things. Sometimes it’s ambiguous — is this a date? Sometimes it’s coolly non-committal. Sometimes it’s a Tinder thing and you’re confused whether there are aftermath expectations. Maybe it’s an agreed-upon FWB or NSA situation and you’re both already so comfortable that you don’t need to dress up. You could still be feeling it out for yourself, uneager to play your hand too early, or disagree with the aesthetics of “serious dating.” All of these and more are very real and nuanced aspects of contemporary dating life (navigating tone, attraction, and social cues is not the same thing as “game,” which is manipulative and often shitty) With all that said, we think you should take first dates to Ruski’s (212 Danforth St.), an authentic neighborhood bar. We like that it’s loud and bustling without being too disruptive to casual conversation, and it’s about as low stakes as it gets. Now that the tourists have finally left them alone after that absurd Bon Appétit article, you and your kinda-sorta date can chill in peace over a plate of decent nachos at one of their awkwardly tall tables. If you’re not into that, we also recommend The Snug (223 Congress St.), an East End classic because its row of intimate cabin-like private “snugs” achieves a sort of conversation space that no one else in Portland can offer. The Old Port’s Mash Tun (29 Wharf St.), a beer bar with occasional gestures of sports appreciation, offers a lively and only partly Old Port-y setting, yet numerous places to slink away and converse. And Arcadia National Bar (24 Preble St.) is a good one too. It attracts a certain set — maybe you don’t want people yelling at one another for Catan resources during your first date? On the other hand, it can also be refreshing to see people doing things besides getting drunk.


Mash Tun [Photo: instagram/mashtunportland]

Dinner: Yobo (23 Forest Ave.) is run by a couple (Sunny and Kim), and if you listen close you can hear their salty banter as they manage the dialogue between kitchen and dining room. The very name “Yobo” celebrates the tart pleasures of love — its a Korean term of affection that is a tad sarcastic. The room has low light and an intimate feel. Yobo’s banchan are the perfect first date appetizer — gorgeous little bowls with a variety of flavors worth talking about when other conversation lags: you might get chewy, fishy-hot anchovy jerky, daikon served many ways, soft and pale baby braken fern, hot garlicky parilla leaves or candied black beans. 

Activity: There’s a short list of conditions you want from first dates. You want something low stakes, but still serious enough to show you’re not about to split after drink one. You want an activity that stretches the comfort zone ever so slightly without throwing either of you off. And you want to immerse yourselves in something that you can talk about afterward. Is that contra dancing? For some, it sure as shit is. Portland Intown Contra Dance throws it down every Thursday at 7:30 pm (though notably not on February 21) in the West End (159 State St.), and you can show up at 7 pm for a beginner’s lesson to shake the clumsies out. Trust us here. We get that contra dancing isn’t for everyone, at least not at first blush, and there’ve been times in our own lives that we’ve rolled our eyes at the suggestion of doing this with someone we actually like. But it’s 2019. You’ve totally been playing with your phone all winter (don’t tell us otherwise), and there’s no better way to find out if you wanna get close to someone than to practice putting yourselves in a strange physical space with them. Swing your partner round and round — what else is there, really? 


Drinks: There’s a whole class of people who go to the Top of the East (157 High St, top floor) without their tongues planted firmly in their cheeks, but let’s face it: they’re not reading this paper. We think this place can be weird, but it’s always interesting. The cocktails are good, it’s fantastic people-watching, and being up there is so bizarre that it immediately serves as its own icebreaker, which can give you and your date the sensation of being on the same “team” early on. (“Wow, this place is something, huh? Wanna go somewhere else?”) Remember, first dates are all about memory-making. 


Chef's choice sashimi at Izakaya Minato [Photo: Erik Neilson]

Dinner: Omakase at Izakaya Minato (54 Washington Ave.). This works beautifully as a fairly upscale ($30 per person) first date. Expect a sequence of delicious things to react to together that neither person has the responsibility of having chosen. The only things you have to choose are the sake and your individual sake cups — a nice touch, plus noticing which cup your date chooses could reveal all kinds of useful predictive personality nuance. 

Activity: Going to see a play can also be fancy-as-hell first date. It requires some measure of planning, more than popping in to see something at the Nick, which shows you’re kinda serious, and then you’ll have more to talk about afterward too. There are plenty of exciting shows are up over the next month (check Megan Grumbling’s previews elsewhere in this issue), and in a city as small as this, one of you are likely already Facebook friends with one of the actors.



Drinks: For the long-term couple looking for some casual drinking, we say forgo the bar and go smelting instead. Nothing like renting a fishing shack with a loved one (and maybe a cluster of other friends too) as you stare into the dark crystalline void where your fishing line plunges into a frozen lake ... for hours. Split a bottle of bourbon, play a few pointless games, let the pleasantly encroaching boredom remind you of stories you never thought you’d share, cook up a few fish along the way, and fall the hell in love again. We’d recommend Jim’s Camps (4 Bowdoinham Rd, Bowdoinham) as they’re not that far, but there’s about 10 of them within a couple hours, so take your pick. You never know which week the ice is gonna thaw, so make plans ahead of time. It’s classic Maine fun.


The Treehouse [Image: facebook/The Treehouse]

Dinner: One of our absolute favorite off-the-beaten-path restaurants is The Treehouse (484 Stevens Ave.), a casual fine dining restaurant in an otherworldly designed space above Pat’s Meat Market in the Deering neighborhood. The folks here put a ton of effort into decor and design, bedecked in soft-colored string lighting, wood interiors, and plants stretching their muscular vines around the earthen arches and columns. The result is an ambiance 180 degrees from the cold, lifeless frost you’ll find outside. The food is pretty wonderful too — a Greek-influenced menu of New American offerings and hearty flatbreads (and fantastic mussels). Entrees run roughly $17-25, but it’s also plenty of fun to gorge on flatbreads and apps in the $9-12 range.

Activity: One of the beautiful things about aging with someone is watching them slowly lose their physical grace. It offers countless moments of shared humility — “wow, bodies are crazy, huh!” — and a wide-open avenue for compassion. If you and your partner are really meant to be, you’ve also mastered the art of making fun of each other when you slip on the ice. (Metaphor alert!) A night of community ice skating at The Rink at Thompson’s Point offers all this and more, and you can wind down with plenty of cutting-edge drinking options right across the street. But act fast. The ice skating rink is only open until February 24.


Drinks:  If you wanna get out of town, it’s hard to beat Frontier (14 Maine St., Brunswick), that eclectic restaurant and multipurpose art spot. Pull up to the bar, order a couple of Rita Hayworths (Ancho chili & hibiscus tequila, Cointreau, house sour, and lime), and let those reflections on life and love fly

Dinner: You obviously won’t be able to snag a dinner reservation in this category for 2/14 itself (which is, after all, a day after this issue hits the streets), but there’s nothing about Valentine’s Day that doesn’t apply to the rest of the month, or March as well. In that case, making a dinner reservation at Fore Street (288 Fore St.) the mother of all Portland restaurants, is in order if you’re going anniversary-fancy. Most of the other top restaurants in town have more of a summery vibe, and the hearth heat of Sam Hayward’s kitchen still makes for essential Maine dining. If you miss out on a reservation, get there early (they start serving at 5 pm) with your loved one and snag a couple seats at the bar.


Petite Jacqueline [Photo: Erik Neilson]

Or! Is anything more romantic than a giant hunk of melted cheese? Take your boo to Petite Jacqueline for raclette, a beloved European dish traditionally made by heating a wheel of cheese over a fire and then scraping the warm, gooey goodness over bread. $60 gets you all the hot cheese you can handle with an array of delicious complements and fixings for two. Just remember to plan ahead — PJ requires 24 hours' notice for this delicacy.

Activity: If you’re a well-resourced couple doing something fancy in February, don’t (just) go to dinner, go away. It’ll be far more meaningful to rent a yurt for a couple nights than to join the carousel of 90-minute meals that Portland restaurants churn out over Valentine’s Day (and Maine Restaurant Week, fast approaching the first week of March). Maine Forest Yurts (430 Auburn-Pownal Rd, Durham) is fully booked the next couple weekends, but what better expression of romantic longevity could you give your partner than to present them a reservation for a getaway yurt weekend during the April thaw? 



Drinks: There are friends who drink beer together, and there are friends who drink cocktails together. (Wine is often a different story.) If you’re the former, we suggest you head to Salvage BBQ (919 Congress St.), where there’s often trivia (Wednesday) or bingo nights (Sundays) to keep things fresh. If you’re the latter, we’ll push you to another BBQ joint — Elsmere BBQ (476 Stevens Ave, 448 Cottage Rd, South Portland), which cares a bit less about brews and prefers an elevated approach to cocktails, particularly for a place that also serves burnt end nachos.

Dinner: Depending how you play it, a winter date night at Bonobo (46 Pine St.) can be comforting, chill, romantic, or and fresh. It feels like the entire city’s food scene has changed six times over since this place first began, and as a result, it’s one of the very few “old Portland” restaurants remaining. New ownership hasn’t changed that, there’s still a thoughtful selection of local beers and wine (with solid happy hours and pizza specials Monday through Wednesday), and it still has the sort of low-key vibe where it’s possible to bust out a game of Bananagrams while you split a bottle of Sangiovese.

Activity: Gather your pals for a night at 33 Elmwood (33 Elmwood Ave, Westbrook), a restaurant and bowling/bocce alley. There’s plenty of light even in winter (which keeps spirits up, y’know?), and the lovely wood interior makes for a nice change of pace to the raucous, digital-heavy vibes of other area bowling alleys. With a full menu of thoughtful pub food (tofu grain bowl, mac ‘n’ cheese, pastrami welsh rarebit melt sandwiches, the works!) 14 bowling lanes and four courts used for bocce or cornhole, there’s plenty for you and your friends to do, and some opportunity to bump into someone who — who knows — might become your next Valentine.


Eaux [Photo: Erik Neilson]


Drinks: We wouldn’t necessarily call this “fancy,” but it’s about as upscale as two nonromantic buds have cause to get. Regardless, we’re somewhat obsessed with the New Orleans cuisine over at Eaux, and doubly obsessed with their oddball postmodern programming (seriously, a winter “Seinfeld-themed dinner” at a Cajun-inspired restaurant just doesn’t compute ... therefore it’s genius!). If you and your friend get off on these kind of IDGAF vibes, head over to their next one on February 20, where they host a “Prohibition Dinner” paired with beers from Goodfire Brewing Company and fishy offerings from Mr. Tuna, a sushi food cart often found in the Public Market. Nothing inspires great cocktails so much as the dim cultural memory of not being able to drink them. 

Dinner: For the friend date, we love Asmara (51 Oak St.), the authentic Eritrean restaurant in the Arts District. Asmara occupies a spot on the Venn Diagram that connects unpretentious, no-frills dining with an experience that’s pretty atypical and unique (at least for most Americans). The food here is undeniably delicious (and vegetarian options abound), and very little compares to the actual sensory experience of eating here. Sharing a huge plate of injera (a spongy, sourdough-risen flatbread that serves as both plate, spoon, and meal itself) is both messy and pleasurable. It’s fun, good for you, and provides plenty of conversation fodder. However, it’s not an ideal meal for those who plan to jump under the covers later — that injera has a tendency to expand in your stomach, which might make you wanna chill a little too hard. 


"Huggins No. 22," from Relational Undercurrents at the Portland Museum of Art

Activity:It’s maybe a little boilerplate, seeing how it’s one of the city’s primary arts institutions, but a weekend friend date at the Portland Museum of Art (7 Congress Sq.) can feel really ... uplifting? illuminating? grounding? (Hey, it’s your personality.) We say “weekend” because that’s when you can most easily pair your art consumption with a film — this month, the Oscar-Nominated Short Films (available in Documentary, Animation, and Live Action flavors). We’d recommend seeing their new exhibition “Relational Undercurrents: Contemporary Art of the Caribbean Archipelago,” curated by Tatiana Flores and described as a “holistic and multifaceted exhibition that repositions the cultures, voices, and artists of the Caribbean islands.”



Drinks: The solo casual night of drinking could go a lot of different ways. Are you looking to bump into people? Try LFK (188A State St.). Are you looking to get drunk by yourself? Start at Amigo’s (9 Dana St.) and see where the night takes you.


CÔNG TỬ BỘT [Photo: Erik Neilson]

Dinner: We're huge fans of the contemporary Vietnamese restaurant CÔNG TỬ BỘT (57 Washington Ave.), one of the best and most rewarding dinner experiences in town. Our own Erik Neilson wrote that “the space is lively [and] the menu is playfully self-aware” in an opening-night review in 2017, and they’ve only improved since. Sit at the bar, maybe with a book, and take your time with their HỦ TIẾU XÀO, a spicy stir fry of rice noodles with chilis, Chinese broccoli, scallions, peanuts, and red-eye brown sauce. As a bonus, CÔNG TỬ BỘT pairs with the Brooklyn-based social group Queer Soup Night on February 24, a community meal that benefits the harm reduction group Maine Access Points and LGBTQ youth organization Portland Outright, both vital frontline organizations doing justice work in Portland.

Activity: Casual solo activities expressing self-love ... hmmm, can’t think of any! JK, there are tons of body-based activities you can do in this arena, from hot yoga at Maine Hatha Yoga (49 Dartmouth St.) to rock climbing at The Salt Pump (36 Haigis Parkway, Scarborough). You might also check out the “Yoga for Sustainable Activism” class every Monday at 5:30 at Portland Community Squash. The class is a special series of free yoga intended for those working in social justice to avoid burnout, and “to strengthen resiliency, compassion, clarity, health, and well being of self and community.” A convo about self-care and social justice activism follows each class.

If you’re good on the exercise front and want to work your finer sense of aesthetics, Engine (128 Main St, Biddeford) hosts a “Drink, Draw, and Meet” on Valentine’s Day itself, February 14, where those who are not paired up. It’s a night designed like speed-dating, but instead of talking awkwardly to someone sitting across from you, you’ll be drawing them (not nude, but for those interested in that angle, the next figure drawing class is February 26)! They switch chairs every two minutes. Sounds ridiculous — which won’t be lost on anyone participating — and that might just be the thing. 


Drinks: Going out drinking alone can be tricky business. It’s better to do it in a place you can savor than a dive bar. For this, we think that Bramhall (769 Congress St.) has the right mix, excellent cocktails and a classy speakasy vibe. It’s a classic date-night spot, but the bar space is substantial and private for those who wanna do their own thing, and they often seem to have spur-of-the-moment deals and whiskey tastings.  


Chaval [Photo: Erik Neilson]

Dinner: Taking yourself out to a fancy dinner is a time-honored art. Obviously you’ve got to listen to your value system here — do you want something you’ve never tried? An old standby? Somewhere you can be around people but not have to talk with them? Valentine’s Day proper is couples-central, but the rest of the winter offers prime real estate for staking out your post at the bar or a small table of one of Portland’s finest. For this sort of thing, we like Chaval (58 Pine St.) in the West End. They’ve got two types of seating for solo diners — the bar and the “community table” — and the convivial neighborhood vibe of cheery West Enders, many of them older, makes for a nice ambiance. As a menu, it’s spectacular — their truffled deviled eggs and North Spore mushrooms with duck egg are fantastic appetizers, and the Mussels a la Normandie entree is a perfect antidote to the Maine winter

Activity: The sensory deprivation tanks at “relaxation spa” Float Harder (500 Washington Ave.) offer an experience unlike anything available in nature (at least in the winter), and while this writer hasn’t tried it, a number of folks have told me that they find it incredibly healing (not your typical woo woo types either). You can opt for a float pod or float room (big enough for two, actually). Valentine’s Day has a ton of weird gravitational pull, not all of it in directions that feel good. These folks are ready to release it. Submit to that #tanklife!

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