Valentine’s Day approaches and for those on the dating scene, words from Max Ehrmann’s 1927 poem, Desiderata, may help inspire: “Neither be cynical about love; for in the face of all aridity and disenchantment, it is perennial as the grass.”

Obviously, Mr. Ehrmann did not live on Martha’s Vineyard.

Dating can be challenging in any context, but it’s especially so for people living on an Island, where even the presence of an extra car in the driveway draws attention.

“MV lacks the anonymity that a city has that allows that kind of shameless romance,” a young Islander said in a Facebook message. “If you make a fool of yourself, you will probably see that person again in the next day or two and they probably at least know your parents.”

It can be hard to take a chance in an environment like that. Advertising algorithms also illustrate how difficult it can be, with sidebars on internet browsers that entice Vineyarders to meet “hot singles in Noman’s Land.”

For some Islanders the pool is so small the ferry helps bridge the gap. — Ray Ewing

Islanders from musicians to librarians bemoan what they perceive to be a claustrophobic scene, made startlingly apparent on various dating apps, where almost everyone you match with on Tinder went to your high school.

“To date, you need to import,” one person said.

Given the limited pool, it’s not uncommon to take the ferry to get to a date.

“It starts small,” one young researcher from Woods Hole said in an email who dated an Islander for awhile. “You’ve burned through all your potential Tinder matches. You expand your search radius by a mile. Just one harmless mile. Then it’s another mile. Then another mile. Eventually, you’re matching with people ‘on the other side.’ The idea that a ferry would be too burdensome seems like a luxurious thought from the very distant past.”

The consensus is clear: it’s a small pond, annoyingly so. The mere mention of dating draws eye-rolls among young people at the Ritz in Oak Bluffs. And winters can be taxing for young people here, single or not.

According to 2014 census data, there are more than 2,300 people in Dukes County between the ages of 20 and 34. For those people, forming connections is not a luxury; it’s a necessity. To retain them, the Island will need to facilitate those friendships.

That’s the thinking behind a new initiative, OysterMV, which aims to provide a space for people in their 20s and 30s year-round. It’s not a dating initiative, but rather a reason for young people to leave the house, especially in winter.

“The Island presents certain challenges to that age group,” said Alex Bullen Coutts, who leads the project. “With the seasonal flux, there is an inclination to hibernate and isolate in the off-season.”

A new initiative, OysterMV, aims to provide year-round opportunities for people in their 20s and 30s. — Ray Ewing

OysterMV launched early this year with the slogan “Your Island, your way.”

A major focus is connecting existing organizations with young people. At a focus group for the program, Ms. Bullen said one young woman shared her experience of wanting to see a snowy owl and going on guided hikes where she found she was usually the only person from her age group.

“There are so many young people here who love hiking and doing things outdoors,” said Ms. Bullen Coutts. “We just need to help them find one another.”

OysterMV has offered hiking excursions with The Trustees. They’ve also organized hot drinks and tarot card readings at Not Your Sugar Mama’s, free admission to a performance at the Yard, and a free monthly film series with the Martha’s Vineyard Film Center. All are promoted on an active, emoji-laden Instagram account:

“All these organizations are already chomping at the bit to do things like this,” Ms. Bullen Coutts said.

Upwards of 30 people attended the group’s most recent event at the film center, a Tuesday night screening of Wes Anderson’s The Royal Tenenbaums and a corresponding costume contest.

But despite the challenges of finding love on the Island, it continues to happen. Islanders Garrett and Marisa Burt met on Tinder in 2014, in the middle of winter.

Marisa is a native Islander. Garrett spent summers here as a kid and moved here full-time when he was in middle school.

“I think you can be totally surprised here at who you don’t know,” Mr. Burt said.

Marisa, an architectural designer, said she feels “very lucky” to have met her partner. “It’s definitely difficult,” she said of dating on the Island.

They first made the jump from Tinder messages to real life late one night right before Marisa left for a trip to the mainland. Garrett dropped by her house and they spent half an hour talking in her driveway.

They started dating regularly that summer.

“One of the first more substantial dates we went on, we definitely ran into a bunch of people I knew right away,” Mr. Burt said. “You sort of just roll with it.”

The two became engaged on Christmas Day in 2016 and were married in September of 2017. Mr. Burt said being committed to another Islander made building a life here much more likely.

“To be in it together makes that prospect make a lot more sense,” he said.