Features

By Jonathan Soroff

Being unattached has advantages. You can eat dinner in your underpants. You can sing country music, badly, without fear of reprisals. No one will judge you for watching Hoarders.

Another plus: You might meet someone like the 20 singles presented here, in our annual roster of Boston’s most desirable bachelors and bachelorettes. As always, there are 10 men and 10 women. As always, we fashioned our list from reader nominations and the highlights in our own address books. The result is an eclectic group of accomplished, appealing, unmarried people—which isn’t to say that they’re necessarily desperate to hear from you. They all have busy schedules.

And they all have our approval, being fun, talented Bostonians who’d shine at any flirtatious cocktail soiree.

Here, then, are Boston’s Most Eligible Singles, Class of 2011.

Tom O’Keefe
(aka BostonTweet), “21+”, internet entrepreneur

Born and raised in Poughkeepsie, N.Y., he came to town to study politics and economics at Boston College before working as a financial analyst. Then he shifted gears and started five different Internet companies over the past 11 years. The latest is a Twitter-based information source about all aspects of life in Boston, and has attracted 25,000 followers. He’s the local rep for the collective-buying behemoth Groupon and the founder of a new venture called b.social. Cycling is his only distraction from the digital world, but since he eschews cars and public transit, he regularly logs 10–15 miles per day by foot. A devoted music fan, he’s seen U2 live 34 times and owns four guitars, none of which he plays particularly well. Through his online presence he’s been able to create awareness for several charities, for which he also volunteers. Among them: the Greater Boston Food Bank, Community Servings and the Home For Little Wanderers. Interested ladies had better not be allergic to cats—he owns one named Jara, a rescued animal from the MSPCA.  

Kara Hurston
25, hair stylist

Our lesbian bachelorette belongs to a splinter faction of hipster haircutters who abandoned Newbury Street to create the South Boston salon Shag. A North Shore native who grew up in Rhode Island, she studied cosmetology at the Paul Mitchell School and boasts some of the city’s edgiest trendsetters as her clients. No wonder, since she’s one herself. She’s often pressed into service for fashion shows and editorial shoots, and this past fall she officially “arrived” by working Fashion Week in New York. While she’s influenced by fashion icons like Edie Sedgwick, she approaches styling hair the way a painter approaches a canvas—and she approaches canvases that way, too, since she’s an artist in every sense. Soccer has been both a passion and a strength; she’s competed at the national level and in tournaments all over the country. Nowadays, she loves scouring thrift stores for vintage clothing and furniture. The Yorkie/poodle mix to whom she’s utterly devoted is named Mae. When indie filmmakers look to cast the super-cool iconoclastic dream girl, she’s their Platonic ideal. 

Erin Sullivan
30, tax manager

This Midwestern lass earned two advanced degrees (a JD and LLM) and works in the tax department of one of the world’s leading private investment firms (with roughly $65 billion under management). She’s a born athlete and will be running her second Boston Marathon this year, while she also waterskis, surfs and has recently taken up skiing. While keeping up with her monthly book club, she loves to travel (a trip to the Amalfi coast is in the works for this summer) and she attends as many live music performances as her schedule will allow. Her quieter interests include amateur photography and WWII history. Despite living alone, she shops at Costco, and the surplus rolls of paper towels in her oven are an indication of how often she cooks. Her hectic schedule includes extensive charitable work for Multiple Sclerosis and other causes. An Ohio girl through-and-through, she smiles at strangers and actually waits for an answer to “How are you?” Hot dogs, sports and American beer are her idea of a good time. She’s also highly ambitious: She keeps “bucket lists” for every year and every decade of her life, and has already checked a great many items off (although the sky-diving scheduled for October will now have to wait for spring). One caveat: She’s a practical joker. Anyone who’s interested had better bring his A-game.

Jason Cheek
30, sous chef

A Southern gentleman in the best sense of the term, this North Carolina transplant serves as the trusted second-in-command to his friend Josh Buehler at KO Prime. Cheek moved to Boston three years ago and loves the city despite his ongoing search for a good pulled-pork sandwich—which explains his enthusiasm for his restaurant’s weekly “Nose to Tail” night. In his spare time, he likes sampling new whiskeys, watching sports (he’s a committed ACC basketball freak) and eating as much good food as possible. He also likes to draw, although he considers cooking its own art form. In addition to his involvement with the Slow Food movement and National Farmer’s Association, he supports KO Prime in its work on behalf of Autism Speaks. He was named best new chef in 2007 by the News and Observer for opening the restaurant South (in North Carolina). Even better: He’s won two wing-eating competitions. Most impressive of all, his upbringing hardwired him to treat women with courtesy and respect: opening doors, pulling out chairs… Rhett Butler has nuthin’ on him.

Sonya Cosentini
32, PR executive

A spunky go-getter, she studied journalism and public relations at Emerson College, where she was class president and graduated summa cum laude. She now works as manager of media relations and spokesperson for TJX. Her job requires everything from working with celebrities and coordinating fashion shoots to appearing on national TV to discuss seasonal trends. An avid reader, she can be found at the library or in a coffee shop with her nose in a book. She’s learning to cook from her Italian grandmother, and she’s developed a passion for running (4–6 miles a day), as well as for pilates and yoga. Even though she’s an intrepid traveler, she loves the charm of home and often visits her family in western Mass. On the charity front, she raises money for domestic violence prevention and impoverished children, most notably through Save the Children. A delightful mix of determined and down-to-earth, she’s an overachiever who makes it all look effortless.

Omar Thomas
26, assistant professor

Our gay bachelor is an assistant professor of harmony at Berklee College of Music, where he teaches music theory and chairs the LGBT alliance. Raised in Delaware, he earned his M.Mus. from New England Conservatory but has been composing and arranging since the age of 12. His 17-piece jazz band, Omar Thomas Large Ensemble, will release its first album, I Am, in mid-2011. An active spirit, he jingles his bells for charity in the annual Santa Speedo Run. Otherwise, he loves ’70s soul music and a good cocktail. A member of the Fenway Health Board of Visitors, he also belongs to ASCAP, which gave him its Young Jazz Composer award in 2008, and he was nominated for Jazz Artist of the Year by the Boston Music Awards. His biggest inspiration is Billy Strayhorn (Duke Ellington’s openly gay pianist and arranger), and we’re willing to bet he’ll someday be an inspiration for future jazz greats himself.

Kimberly Walleston
24, fashion correspondent

This New Hampshire girl jokes she was raised in the mountains by wolves, but she turned out awfully polished. Besides graduating summa cum laude and as a member of both the Alpha Chi and the Lambda Pi Eta Communication honor societies at Colby-Sawyer College, she won an award for writing a series of children’s books on environmental literacy. Now she works as the host of “Fashion Forward” on Styleboston, which airs on WCVB-TV Channel 5. Her job requires her to troll through the city’s boutiques and to hang out at glamorous fashion events—in other words, to do what a lot of other people do for fun. In her time off, she enjoys hiking, camping and snowboarding in the White Mountains, and cooking with local, organic food. A multimedia artist, her most recent work was a charcoal, acrylic and watercolor cityscape of the Dubai skyline. She’s a big fan of watching Boston sports. On the participatory side, she played volleyball in high school and danced (mostly jazz and hip-hop) throughout childhood and college. Her skill in Brazilian jujitsu gives her confidence to tackle the rowdiest barroom. Oxfam America and various environmental initiatives keep her active, as do her five dogs—four rat terriers and a Yorkie. A refreshing balance of urbane sensibility and rural values, she might buy a lot of shoes, but she never forgets the pleasures of bare feet.

Jennifer Glickman
29, interior designer

After studying art history at UVA, she received an M.A. in interior design from Suffolk University, while a grad school stint in Florence, Italy, offered a thorough immersion in art and architecture. As a freelance interior designer, she works for universities, libraries, residences, commercial spaces and restaurants. Her most recent project: Isabelle’s CurlyCakes, the new Beacon Hill cupcake shop by Todd English’s daughter. Her passions include Bikram yoga and running, but having grown up in the Virginia countryside, she loves everything about the outdoors. She sketches to relax, and she sometimes drops in on figure-drawing classes. Not surprisingly, she spends most of her disposable income on furniture finds and is an unapologetic architecture nut. She’s a member of the Boston Society of Architects, and this year cochaired a committee that organized a fashion show for the International Interior Design Association. Her half-Korean, half-Russian background boasts the added flourish of a Southern accent. She’s like a hothouse flower that can handle the toughest terrain.

Jared Banner
25, amateur scouting coordinator for the Red Sox

The name alone has a superhero sound. Growing up in Brooklyn, he was a state champion wrestler in high school before switching to baseball at Amherst, where he got a B.A. in psychology. As a coordinator of amateur scouting for the Red Sox (he might’ve grown up a Mets fan, but he’s a loyal citizen of the nation now), he spends most of his time traveling in search of the next Dustin Pedroia or Jon Lester. His hobbies include Bikram yoga, boxing and pickup basketball, while his taste in books tends toward nonfiction. Hailing from the land of Jay-Z and Biggie, he likes to end a night on the town wherever the DJs spin the best hip-hop. A member of the advisory board for the charity Smallbean, he also participates in the Susan G. Komen Race for the Cure. He was only 22 when he received his first World Series ring. If you’re the girl he likes enough to put a ring on, expect something on the conspicuous side.

Ben Dolgoff
25, tech entrepreneur

This Hyannis boy cofounded Peekaboo Mobile, a start-up that developed an app that uses your smart phone’s GPS to find nearby discounts—flash the cashier your cell and claim the savings. Dolgoff contemplated a career as a pro golfer, studying “professional golf management” during his first year in college down South, before earning a finance degree from Suffolk University (where he still captained the golf team). A volunteer at Rosie’s Place and the Greater Boston Food Bank, he likes running and tennis, but when work and weather permit, you’ll find him at the beach. He’s an avid networker on the start-up scene and often speaks on “mobile expert” panels. He calls the North End home and would rather do just about anything than veg on the couch. Added bonus: If you split the check on a date with him, you’re guaranteed to get the best possible deal.

Gina Patterson
26, victim/witness advocate for the BPD Homicide Unit 

The real-life version of those hotties on Law & Order, she works as a liaison between homicide detectives and victims’ families to ensure they receive the resources, support and information they need. At Simmons College, she double majored in biopsychology and women’s studies. While living abroad, she published articles in the book Women to Women: Young Americans in South Africa, and she’s currently considering a master’s degree in social policy. A dedicated foodie, she blogs her reviews on Youngsophisticatedfoodie.wordpress.com, practices meditation and yoga, and is broad-minded enough to enjoy both Real Housewives and NPR. Because her parents are from Jamaica and Trinidad, she attends the annual West Indian carnivals in Boston and New York, dancing with abandon to soca, reggae and the steel pan. She teaches classes at a domestic violence shelter and belongs to Alpha Kappa Alpha (the oldest African American sorority), as well as to Catalyst, an organization at the MFA. She also serves as Alumnae Class President at Simmons. In short, her sense of social justice isn’t her only beautiful trait.

Mike Young
30, concert promoter/photographer

Picture the guy in High Fidelity if he had a high-powered job in the arts and was actually cool. As the director of concert marketing and promotions at the Citi Performing Arts Center, he’s worked with everyone from Yo Gabba Gabba! to Lady Gaga. The closest thing he has to an addiction is photography, especially of live concerts—he’s been spat on, tackled and found himself as the only obstacle between an artist and 20,000 rabid fans when the barricade collapsed. He wields a camera like a networking tool, an easy icebreaker to strike up a conversation with anyone. Vintage equipment is especially to his taste because he likes the idea of capturing history with something that’s a piece of history itself. In guest DJ gigs for Weekly Wax at River Gods (under the name Young DMC), he indulges an obsession for playlists. His vacations tend to feature places with exciting mountain roads; not surprisingly, he loves cars. Since he’s a movie buff, too, drive-ins are his idea of heaven. He runs and practices yoga to stay in shape, and is actively involved in the Epic Man project, which raises money for charity. This epic man is all about art, intensity and a sense of adventure.

Bonnie Cardillo
30, designer, stylist and wardrobe consultant

It’s rare to meet someone who both lives for fashion and who’s down-to-earth and approachable. A visual merchandising manager for the upscale preppy shop Vineyard Vines, she also owns Style101, a wardrobe consulting business, and designs jewelry for her own brand. She enjoys dancing, antiquing, reading, shopping and anything sports related. A natural athlete, she plays golf and tennis, runs, skis, hikes and is learning to sail. On her travels abroad, she collects vintage postcards, and through the UVM Young Alumni Committee, she volunteers with organizations like the Charles River Cleanup, the Pine Street Inn and the Women’s Lunch Place. She’s also an MSPCA-Angell donor. A born explorer, she backpacked solo all over Europe, and if she didn’t love her work, she’d travel nonstop. A dynamo with looks to boot, most guys would need daily vitamin B shots just to keep up.

Brad Marchand
22, pro hockey player

The Bruins’ Number 63 may not be the biggest bruiser in the NHL (he’s 5'9"), but he’s as scrappy as they come. Even so, he’s a gentleman when the skates come off. Born and raised in Nova Scotia, he represented Canada twice in the World Junior Ice Hockey Championships (2007 and 2008), helping to bring home the gold both times. The Bruins drafted him in 2006, and he made his National Hockey League debut in 2009 against the Nashville Predators. His off-ice hobbies include gaming (he’s an Xbox aficionado), movies and dining out. Aside from hockey, this all-around sportsman plays golf and tennis, enjoys hunting, fishing and spending time by the water. He participates in numerous charity golf tournaments and pays frequent hospital visits to lift the spirits of patients. Any interested woman must love dogs; he owns a husky/shepherd mix. An added bonus: So far, he still has all his own teeth. 

Jennifer Canesi
28, nurse practitioner

A hotter, hipper version of Florence Nightingale, she graduated summa cum laude from Boston College in 2005, and with honors from a master’s program at MGH. She now works as a nurse practitioner in aesthetic dermatology, which blends her lifelong love of medicine (she comes from a family of doctors) and her passion for art. Raised in Foxborough, she has season tickets to the Patriots, but she’s also an impressive athlete herself. Spring triathlons and road races keep her active, and she’s run the Boston Marathon. Proving her generosity and inventiveness, she arranged a giving program that allocates a portion of her salary to a different charity each month. She’s also a member of the American Association of Aesthetic Medicine and Surgery. Beauty, in her case, goes a lot more than skin deep.

Michael Haruto Oshima
(aka DJ Sankyu), 24, judo instructor and DJ

He was raised in Boston but went to Tokai University in Japan and then Harvard, where he earned a B.A. in linguistics (in other words, he can quote Chomsky). He also won the 2009 Collegiate Judo National Championship. In addition to teaching at the Tohoku Judo Club, he blogs, writes and spins music. Mashups are an interest, as are Italian Renaissance art, calligraphy, soccer, filmmaking and the writings of Japanese author Haruki Murakami. On the flip side, he enjoys strange and/or zombie movies, offering dubious advice and mah-jongg. He’s also got a subversive sense of humor: When asked about his interests, he lists “polyamory,” “narwhals” and “bacon,” and he identifies one of his talents as doing a good impression of Stitch from Lilo & Stitch. In addition to English, he speaks Japanese, Portuguese and Spanish. In the future, he wants to write and direct a film. Or have one made about him. 

Abe Donner
33, sneaker executive

This Duke University graduate is the Latin America manager for New Balance sneakers. In addition to mastery of the secret workings of the athletic footwear business, his job demands an intimate understanding of Latin American culture—so even though he’s a gringo, he can do the Latin lover thing. Previously, he worked at Nike, which sent him to Buenos Aires, Argentina, to manage its soccer apparel business. He’s an avid runner who also enjoys cycling, waterskiing, downhill skiing and golf. A doting uncle to his two-year-old niece, it goes without saying he’s a rabid fan of Blue Devil basketball. Any lady hoping to snag him had better keep her passport up to date: He’s visited more than 30 countries, and a passion for pizza has driven him to try and eat at least one slice in every city he visits. Urbane and worldly, he knows not to take himself too seriously. Most embarrassing moment: spilling a bottle of red wine all over himself in front of Matthew McConaughey’s girlfriend, Sports Illustrated swimsuit model Camila Alves.

Julie Scallen
44, lawyer

A high-powered Renaissance woman, she earned a B.A. in French from Wellesley College before getting her JD at NYU Law School, where she was on the Law Review. Since then, she’s risen steadily to become a partner in the corporate department of Bingham McCutchen, LLP, the behemoth international firm. She worked hard to get there, and not surprisingly, she still works hard, but she knows how to let loose. A world traveler, she’s a wine enthusiast who’s still comfortable at a Patriots tailgate (with clients). Climbing to the top means staying in shape, so she swims and practices yoga. A quiet afternoon might find her at a museum or gallery, indulging her taste for modern art. Lest she sound too buttoned-up, she has a passion for fashion and a love of French literature, even at its most avant-garde.  

Trish Fontanilla
27, freelancer

A graduate of Emerson College, where she received too many awards and accolades to mention, she worked at Berklee College of Music as the department coordinator of music therapy. Now a freelancer, she consults on web materials, PR, booking bands, social-media marketing, planning events and writing articles—in short, she’s a Trish of all trades. She loves live music and theater, and is an avid Celtics fan whose heckling belies her innocent appearance. As a musician, she dabbles in guitar, piano and singing, and she’s built her own drum from scratch. Next up: a ukulele. Charity work may be her strongest suit. She’s deeply involved with Boston Cares and was a fund-raising/philanthropy fellow in its Civic Leadership Institute. She also volunteers with Community Servings, Room to Grow, the Friday Night Supper Program, Big Sister Association, Haley House Bakery Café, Boston Living Center and—honestly—numerous others. She estimates that she’s volunteered for 40 local nonprofits since 2002, proving she has a heart as impressive as her résumé. 

Dan Fitzgerald
32, sports retailer

A guy’s guy who’s not a slob, this Tewksbury native studied economics and philosophy at Boston College, where he was captain of the track and field team. With his teammate and best friend, Justin Burdon, he founded the South End Athletic Company, where he serves as a buyer, designer and salesperson. If that weren’t exhausting enough, he operates a personal coaching business and still finds time to surf and snowboard. Attending live music shows is another hobby, and he’s got a penchant for restaurant-hopping in the South End. He and his business partner host numerous charitable events in their store, where up to 20 percent of sales are earmarked for a worthwhile cause. Authenticity and empathy are the traits he values most in others. Any girl lucky enough to land alongside him is guaranteed a genuine mensch.

Credits:

Photos: Adam DeTour

Makeup: Maryelle O’Rourke/Team Artist Rep; hair styling: Lauren Allaby, Oriana Harris and
Jessie Heroux/Marc Harris

Film: TeeDox Films