It’s cuffing season

And if you don’t know what that means, you’re not alone.

IceBrkr founder Kevin Murray was in the running for the 2013 season of The Bachelorette while living on Martha's Vineyard. -Courtesy Kevin Murray

I had never heard the term “cuffing season” until I got a message from the CEO of a startup dating app called IceBrkr.

“I’m a former Vineyard resident who knows how difficult it is trying to date from the Island,” Kevin Murray said in an email to The Times. “Online dating is difficult enough as is, let alone with the Vineyard Sound blocking so many potential matches on the mainland.”

According to Mr. Murray, this time of year is where dating and online matchmaking picks up. Cuffing season starts right about now, and goes into late March or early April. It’s the cold winter months, where single people don’t want to be single. They want to be “cuffed,” or tied down in a relationship, at least through the winter.

It’s true that people on-Island say it’s especially difficult to meet other singles. If you’re a long-time resident, you already know most people, and sort of avoid the inevitable prospect of seeing friends, co-workers, or exes while out on dates. And if you’re new to the Island, it’s really just difficult to figure out where everybody is.

“You don’t really know what it’s like to have problems dating until you try it on the Island in the off-season,” Mr. Murray said.

Mr. Murray is a dating expert. No, really — he has a master’s degree in communications, with a focus on online digital dating. He caught up with The Times to offer advice to Vineyard singles this time of year.


What’s it like to be single on Martha’s Vineyard?

Well, first of all, you rarely move to the Vineyard if you’re in a relationship. In the summer, it’s really free and fun, and there’s a lot going on. But when the fall hits, the days get shorter and the nights get colder, and people spend a lot more time at home. It gets lonely. And with the holiday season right around the corner, you’re reminded you’re single and you’ll have Grandma to answer to at the Thanksgiving table.


What makes dating so hard?

Living on the Vineyard is like being at a high school reunion forever. You want to date, but you don’t want to run into everybody you know. And it’s hard to online date, because there’s a body of water between you and any off-Island connections you make. Dating off-Island also means you have to think about overnight accommodations, which makes everything way more intense than it needs to be.


So what can single people do?

The dating uptick starts right around now. It starts peaking around New Year’s, and keeps growing until Valentine’s Day, which is a fake holiday, but it reminds you that you’re single. If there’s a time to date, it’s now. It’s like fishing. This is when the pond is most likely stocked — this is when you can catch something.

If you’re worried about running into people, you have to get over it ASAP, although I understand. If it’s a first date, try to go somewhere quieter. I brought a girl I met to the Cliffs one January. It was really peaceful and quiet, and no one was out there. I also used to like going to Atria on Sundays, or to the bowling alley in Oak Bluffs. The Loft can be a really fun spot, but you’ll run into people. I also like the Seafood Shanty when it’s open.

If you’re online dating, one hack I use is expanding my GPS parameters. You don’t want to lie to people, but when you live on the Island, your profile isn’t showing up for people on the mainland. Increase your GPS range or change your location so you’ll get a wider range of singles on your feed.


What are some online dating tips?

Whether you’re on Tinder or, don’t lie to people. Choose photos that are accurate representations of who you are. Have one closeup, and one full-body shot. We have these battles with the ideal self and the actual self. No one likes surprises. Build confidence, and reduce uncertainty, and depict yourself as accurately as possible when you’re online dating.

You don’t want to chat online for more than a week or so before meeting. I’ve made that mistake before. And don’t be afraid to meet someone off-Island. Choose somewhere like Falmouth or Hyannis, and stack your dates if you have to. Schedule a date for 1 pm, and another for 3 pm. Squeeze in a Walmart trip if you can.


How does your app, Icebrkr, work? And how can it help people on Martha’s Vineyard?

Well, it’s not an app yet, it’s still in development. But it’s a service that turns your online dating matches into actual dates. We have a team of people who analyze your conversations and photos to give you expert advice on how to build meaningful rapport with your matches and optimize your profile.

We’re currently running an SMS campaign that runs parallel with app development, and that’s something that could help Islanders. It’s a free five-day trial where our team feeds you real-time dating advice. After the first five days, it’s $19.99 per month. We’re hoping the app will launch sometime this January.


So there you have it — dating advice from an expert wingman. Mr. Murray has a passion to help singles mingle on Martha’s Vineyard and beyond.


For more information on Icebrkr, or to give the SMS campaign a try, visit