A few months ago, I boldly ventured out into the depths of a Saturday night alone—and despite my initial hesitation about showing up to an art gallery opening without a companion or five by my side (wouldn’t people think I was weird? pathetic? something worse?), I wound up having one of the most fun nights in recent memory. I felt so inspired by my experience that I wrote about it, procuring a how-to guide of sorts for other like-minded folks who don’t want to wait around on indecisive (and unavailable) friends to keep their social lives afloat.
I’d been out on my own alone at night before my big debut, of course—to movie theatres, cocktail parties where I knew I’d likely bump into a few familiar faces, and other places requiring a minimal commitment to socializing with the unknown—and looking back, I realize that it was the gradual escalation of exposure to situations I’d deemed intimidating that allowed me to waltz into an intimate space full of strangers like I owned the place instead of clinging to a corner, counting down the minutes until I'd permit myself to leave.
Going out alone might not be for everyone, but if you’re intrigued and want to give it a try, here are five places where you can test the waters before swimming out to the deep end, whether you’re single, attached, or just want to try something new. If you feel weird or uncomfortable, you can always go home—but with so many options to explore in this fabulous city of ours, why would you?
110 Brookline Street, Central Square
This is the gallery whose opening I attended and mentioned in my original piece. Blanc is intimate and slightly off the beaten path (you’ll have to head toward Cambridgeport to find it, about a seven minute walk from the Central Square T stop), and hosts opening receptions each time a new exhibit is ready for its reveal (about once a quarter, from what I’ve observed)—replete with a DJ, a (cheap) cash bar and like-minded folks who care about local culture. Add your name to the mailing list to find out about future exhibitions and events.
Piattini Wine Café
226 Newbury Street, Back Bay
There are so many wonderful things I could say about Piattini, a hidden, tiramisu-flavored gem amidst the “see and be seen” restaurants of Newbury Street. But for all intents and purposes here, it’s quite simply an easy place to have lunch (or dinner) on your own, due to its menu portions (piattini means “small plates” in Italian), compact, cozy space and accommodating staff. I recommend the melanzane affumicate—and a generously-poured glass of red wine from their award-winning list.
Wally’s Jazz Club
427 Chester Square, South End
I’ve been to many live music venues on my own before, and truth be told, it can be obnoxious if you’re floating solo in a sea of groups at a general admission show—watch the personal space, people! Wally’s kills two birds with one stone: first, it’s iconic, and despite its unassuming facade, has hosted a series of jazz greats over the years. Second, it’s small—are you sensing a theme here?—and can reach capacity early in the evening, and because seats are far and few between, no one will notice (or care) if you’re standing by yourself or with a small entourage.
279 Harvard Street, Coolidge Corner
Bookworms, rejoice! Brookline Booksmith is the perfect destination if you’re hoping to catch an author’s reading, but don’t feel like subjecting yourself to one of Boston’s many (sometimes, admittedly cliquey) storytelling series. Get on the mailing list, or check the link for a well-maintained calendar of events. Start here and then catch a movie at the Coolidge Corner Theatre across the street, or finish at the Booksmith before a quite bite to eat at the Regal Beagle.
Boston Center for Adult Education
122 Arlington Street, Bay Village
Beyond its many course offerings, the BCAE regularly hosts special events and exhibits (which you can find out about by signing up for the center’s email list or by reading Boston.com, which often includes the events in its A&E listings—or, by signing up for a class). In fact, the BCAE is hosting a photography exhibit (with wine and cheese reception) this Friday in its gallery from 6:00-7:30 PM—and did I mention it’s free? RSVP is required, which you can do here.
A few weeks ago, I met a guy at a concert, and agreed to meet him for drinks several days later. It wasn’t the best date I’d ever been on—we didn’t have much in common aside from our mutual admiration of the musician we’d seen, and it became obvious early on that the chemistry was minimal, if existent at all—but disappointments are part of the dating game, and I chalked it up to experience. When I hinted that I was tired and would probably head home, he flagged down the bartender—and after surveying the tab, slowly peeled off a number of singles to cover the exact amount of his drink before sliding the check presenter my way. To say that I was shocked would be an overstatement (if I were writing a novel about my life, I’d describe my reaction as having “recoiled in horror”), but I was considerably annoyed. Because in my book, the guy pays for the first date—even when it’s something casual—and especially since he was the one who did the asking. (I’m speaking from a heterosexual viewpoint, here.) It’s not so much about the money as it is a manners thing: a guy paying for a first date is one of the few elements of tradition still standing amidst today’s thinly-veiled definition of modern romance. I won’t even do “the reach”—that is, a pretend dive for my wallet that so many women feel compelled to perform once the bill arrives—on a first date (though, as evidenced above, I did so out of necessity on this particular occasion, plus the tip he’d neglected to leave). I will, however, alternate financial responsibility for the tab several dates in, or if a guy’s sprung for a nice meal on dates one or two, I’ll cover post-dinner cocktails—and so on. My rules aren’t hard and fast as much as they are intuitive, and regardless of what my expectations are, I always arrive prepared to pay my way.
I replayed the evening for my girlfriends—some did hilariously recoil in horror—and most etiquette books I own carefully glazed over matters of the heart. So, I checked with the world’s foremost expert on everything, Google, to see if there was any other evidence to support my opinion. The results were somewhat ambivalent, if skewed in my favor:
•LearnVest, a financial website geared toward women, said that it’s a matter of looks, where the more attractive a woman is, the more likely the date would be paid for by her companion—but then again, someone’s perceived level of attractiveness is subjective.
•AskMen said a guy should always pay for the first date, except if the woman did the asking; then, she should pay. (I ran this theory by a guy friend, who shook his head and said that he’d insist on paying even if a woman asked him out.)
•A 2008 study conducted by NBC (which, admittedly, is kind of old in Internet years) netted a mixed bag of gender roles and confusion, leaving the reader without a definite conclusion
First dates are nerve-wracking enough; throw economics into the mix, and thing can get really messy. Still, I remain convinced that tradition has its place here, and that guys should pay for first dates. I'll turn the spotlight to you, readers. Do you favor conventional rules when it comes to paying for first dates, or have you kissed tradition goodbye? Does the type of date affect who pays for what? Was my reaction warranted, or are my expectations totally dated (and perhaps too high)?
Yeah, it’s Valentine’s Day. But let’s cut through the sugar coating, shall we? Sometimes—often—our paths to find The One diverge, and a road trip is in order. And by that, I mean partaking in a good, old-fashioned, American makeout session, which, in my opinion, is among the purest and most enjoyable of carnal pursuits.
But you’re not in a relationship, you say. So what? And you’re not casually dating, and didn't even have a Valentine this year, to boot. Shrug. That doesn’t matter, either. At the risk of sounding like what my high school Latin teacher would call a “floozy,” there are plenty of willing participants out there—in bars, lounges, and other places chock full of dark corners—just waiting for you and your luscious lips to show up. Shake off the idea whether it’s for five minutes or forever—this is about spontaneity! fun! Mr. and Ms. Right Now!—and read on for my favorite places to makeout in the city.
28 Kingston Street, Financial District
Bypass the upstairs and head straight for the basement. Between loud music thumping out of the speakers and the heat from hundreds of bodies packed into a small space, it's a breeding ground for romantic encounters, and reminds me of the basements of my adolescence, minus awkward games of Spin The Bottle. Grab a shot of liquid courage if you must—I’ve found that literally tossing myself against the crowd to get to the bar works well if it’s packed, which it often is—and grab your temporary S/O and hunker down in a plush vinyl booth.
355 Congress Street, Fort Point Channel
Lucky’s Lounge is also a basement of sorts, if you think about it, and maybe that’s why it’s so sexy. Or maybe I just have a thing for basements. In any event, the slight cheesiness of its decor—more vinyl booths, a faux fireplace, an awkwardly-positioned stage—is evened out by an ambiance that makes it seem like anything is possible, and exacerbated by the fact that the bartenders pour their drinks on the stronger side. Also worth noting: Lucky’s is situated at the end of A Street, which feels like an alley, and what’s hotter than making out in an alley? (Cue awkward silence, crickets chirping)
451 Washington Street, Somerville
Dali is somewhat off the beaten path, and totally worth the trip. (Plus, a cab ride can heighten the anticipation, am I right?) Admittedly, it’s a go-to date spot of mine—it’s dark, it’s romantic, it’s delicious—and it’s a restaurant, not a bar. But it’s hard to find a place that serves sangria on tap, and even harder to find a place where the servers won’t rush you out of your table even when there’s a long wait at the door. Plus, everything is served with a wink and a nod—their staff knows what’s up.
Noir at the Charles Hotel
1 Bennett Street, Harvard Square
A hotel bar, to a degree, sets the scene for impulsive moves—like being tipped back into a passionate kiss and coming up for air only to swill from a martini glass before dipping back down again. Noir definitely has a retro je nais se quois that makes those kind of movie-star kisses possible, plus tasty snacks if you’re in the mood to hand-feed the handsome stranger sitting across from you. Even their cocktail names, like “Dark Passage” and “Red Light," seem to inspire a bit of naughtiness in the most unassuming of patrons. Meow.
Enormous Room (R.I.P.)
567 Mass Ave, Central Square
“Hey, wait a minute!” you might think as you scratch your head. “Isn’t Enormous Room no more? Finit? Caput?” Sadly, yes: Enormous Room closed its doors in late 2011 and reopened as Brick & Mortar—which, in its own right, is great. But Enormous Room, with its teak furniture, Persian rugs and shady restrooms, was so cool, it was hot—and that’s why I’m throwing up a posthumous peace sign to one of my formerly favorite places to makeout in Greater Boston; particularly, while pressed against the sink in one of those very restrooms.
Last week, I wrote a response to a New York Times' article, The End of Courtship, and aptly called mine An Encore For Courtship. In it, I heralded interviewee Cheryl Yeoh, whose "Not going to settle for less than I deserve" attitude struck me as refreshing. Yeoh, in return, came across my post—thanks, Google robots!—and shared the response she posted to her personal blog. I've included a link to her reply, and summarized a few of her talking points:
•Women generally prefer men who are considerate and thoughtful than those who try to impress them with material objects.
•It's all about respect: if a man takes a woman out on a nice date, she should thank him and show appreciation, even if she's not interested in going out again. Don't cancel dates at the 11th hour, either.
•It's best to be honest about your feelings early on.
•There's no such thing as a perfect catch, but you should identify what your "dealbreakers" are.
The point I liked the best, which I can most certainly relate to—and I'm sure other women can, too—is this, which I'll quote directly:
"Believe it or not, I’d actually encourage more casual interactions at the beginning of the courting phase: coffee dates, group hangouts, drop ins, etc. They’re all totally valid and fine! But once there’s a clear indication that one (or both) parties, wants to explore something more meaningful, then the guy should make the effort to ask the girl out on a real date. This is the phase where I don’t compromise and will almost never accept last minute texts that sound like this “Hey beautiful. Private dance party at my place. No special attire required.” (actual text I received in Oct 2012) I immediately moved him to my “was promising before but now a loser” list."
So you'll be single on Valentine's Day. So what? It doesn't mean you need to resign yourself to your couch with a box of leftover Christmas chocolates while the Spoken For crowd reigns over OpenTable reservations (unless that's your thing; then by all means, meander away). These events around the Boston area are sure to spark your interest—and maybe ignite a flame with a mysterious stranger. Some require advance registration and/or tickets; be sure to click the links to learn more.
Update! Some of the events I initially listed have sold out. (I told you to check those links!) A few more have been rescheduled due to this past weekend's snowstorm. Check below for subtractions and additions, singles.
Tuesday, February 12, 7 PM - A Night of Love and Secrets with Christopher Castellani and Randy Susan Meyers at Brookline Booksmith, Coolidge Corner
Artistic director of Grub Street Christopher Castellani (A Kiss from Maddalena and The Saint of Lost Things) shares his lauded new novel All this Talk of Love. Meet the Grassos: a family of Italian immigrants who travel back to their ancestral village of Santa Cecilia. Surprising secrets unfold in this warm and witty tale of family and the immigrant experience. Plus: three women’s lives intersect in ways they could not imagine in Randy Susan Meyers’ dark, revealing, honest tale about the aftermath of infidelity. Grub Street Ambassador and author of theThe Murderer’s Daughters introduces us to three mothers, two fathers, and one child - and deep questions about the meanings of love and family.
Wednesday, February 13, 7 PM - Meet Your Valentine with Instinct Matchmaking at Sacco's Bowl Haven, Davis Square
Strike! Bowl your way to romance at this laid-back gathering, with plenty of complimentary pizza from adjacent Flatbread Company and bowling to help break the ice. Cocktails will be available for purchase, too. Be sure to preregister to guarantee your spot!
Wednesday, February 13, 8 PM - Dig Boston's Pre-Valentine's Day #lastminutelove Tweet Up at The Avenue, Allston
We've reached 14K followers, and to celebrate, we want to court you. And drink with you. And let you tweet Sweet Nothings into the ears of your Twitter crushes ... IRL. In addition to FREE beer compliments of Harpoon Brewery, there will be tons of FREE raffle tickets—with prizes compliments of RAWR, ONE Condoms, the Somerville Theatre, Shambala Meditation Center and more!
Thursday, February 14, 7 PM - The Somerville Arts Council presents Nibble at Porter Square Books, Cambridge
Happy Valentine's Day! Join The Somerville Arts Council at Porter Square Books for a virtual stroll through the cultural mecca that is Somerville. Nibble is an illustrated tour through the food landscape of Union Square, with its beautiful, motley mix of pizza joints, mom-and-pop markets, lively pubs, farmers markets, posh new restaurants and brimming global flavor. Nibble captures this dynamic and delicious place with personal stories, illustrations by local artists, and recipes from the featured restaurants.
Thursday, February 14, 8 PM - Anti-Valentine's Day Pizza & a Movie at Ducali Pizzeria & Bar, North End/West End area
Ducali Pizzeria & Bar knows not everyone wants to dress to the nines on Valentine's Day. That's why the pizzeria is bringing out its big screen projector and playing the Jim Carrey classic, Dumb & Dumber, with its full pizza, beer, wine and cocktail menus available for ordering. What better time to pick a pie that's heavy on the garlic?
Thursday, February 14, 10 PM - Tainted Love Industry Party at M.J. O'Connor's, Back Bay
Valentine's, shmalentines! There'll be no mushy stuff at this party, hosted exclusively for the city's industry staffers—the bartenders, barbacks, waitstaff and hosts that will no doubt be serving up their share of kissing couples—with plenty of prizes and giveaways, a $6 late night menu, and drinks on tap from Pinnacle Vodka and Stella Artois. A DJ will spin anti-love tunes, so dance the pain away!
Friday, February 15, 8 PM - The Timberfakes Present: Cry Me A River (Valentine's Day Hangover Party) at the Hard Rock Cafe, Faneuil Hall
Boston's only Justin Timberlake tribute band is back at the Hard Rock Cafe Boston for their annual Valentine's Day celebration. Whether you're single, in a relationship or in between, come shake what your mama gave you with The Timberfakes and their special guests: the charismatic artist known as Elektrik Kidd and the smooth soul sounds of Band 51.
Friday, February 15, 10 PM - Cupid & The Three Kings' Valentine's Bash at Nix's Mate, Financial District
The Three Kings are at it again! Their Valentine's Day bash will feature a dessert bar, a Valentine's-themed lingerie fashion show and a kissing booth (of course). Plus, expert matchmaker Emily Romano of Dateover will be on hand to help the lovelorn find their soul mates. A $20 ticket gets you in (VIP tables are available; acquire via the above link), with all proceeds going to charity. Festive attire is encouraged—think pink (and red)!
Sunday, February 17, 6 PM - Write on the DOT Valentine's-Themed Open Mic at Savin Bar & Kitchen, Dorchester
Bring your best/worst eros-inspired odes, erotica, limericks, diary entries, love sonnets...or seduce us with the work of another author.Hosted by Aaron Devine, with appearances by Sam Cha, Willie Pleasants, Betsy Gomez, Teresa McMahon, Nathaniel Hunt, Lynn Holmgren,Karen Locascio, Karyn Polewaczyk,Theadora Siranian, Lewis Feuer & more! Includes drink and food specials starting at just $4.