Part I: Nobody Just Ends Up Here (Except Barack Obama)

The Secret Service formed an air-tight perimeter; Barack Obama was going to give an address for an elementary school in Martha’s Vineyard, Massachusetts, and no one would be coming in unannounced. No one, that is, except Carter D’Angelo ’17.

See, she was on a mission. Traffic on the sleepy island was utterly gridlocked because of the president. To make matters worse, the chosen elementary school also housed the summer camp where Carter worked.

She was so late you could only blame a matter of national security, so she picked up iced teas for her boss to make up for the delay. If Carter’s father could build their house with his bare hands, she could smuggle two iced teas past the Secret Service. She just had to find a way through the wall of suits and earpieces.

She took a back alley that scurried through a cemetery, then came upon a chain link fence.

“As I was mentally preparing myself to [climb the fence], two men in all black come up with their whole headset and everything, and they’re like, ‘Excuse me, nobody is allowed to be here right now,’” Carter says.

She was speechless.

“There’s nothing innocent that I could say at this point. I couldn’t say, ‘Oh, I’m allowed to be here, I’m just sneaking over this fence … to help children,’” Carter says.

Secret Service: 1, Carter: 0.

Anywhere else, a tea-bearing trespasser facing presidential security would be strange, but on the Vineyard things are different.

Her wacky encounters living in the tourist town include, but are not limited to: partying with Larry David, taking pictures of Justin Timberlake’s butt, and selling a burrito to Seth Meyers. She jokes beaches are full of “piles of crying babies” and that “you can’t go 10 feet without stumbling over a small summer camp.”

But there’s more.

“Everyone kind of just ended up here, if that makes any sense,” she says.

Everyone in this case means, Harvard-graduate landscapers, James Taylor’s avant garde-artist daughter, “crusty fishermen” and liberal conspiracy theorists.

“You can’t be a successful person and live on Martha’s Vineyard, just because there aren’t any jobs there that don’t revolve around tourism,” she says. “So they’re just kind of people who have chosen to live in this beautiful place instead of maybe being successful.”

And as Carter’s beverage-based quest continued, things got as strange as the town where it unfolded.

She was told off at the fence, but she kept going and felt a strange duty to keep the huge teas, even though they were slowing her down.

“I don’t know why, it just seemed really important at the time,” she says.

Then, as entry began to look doubtful, Carter got a call from her boss saying she’d convinced a Secret Service agent to meet with her and let her in.

She reached the main entrance guarded and its line of intimidating state troopers, which was actually less formidable an obstacle. No sneaking, no climbing—all the Secret Service agent there needed was a name and an ID. But remember, this is Martha’s Vineyard, so things didn’t happen like they did everywhere else.

Carter had two problems at this point. First, Carter told the agent, “Sorry, my name is not Carter D’Angelo…because it’s not” (her first name is Margaret). Then there was the fact she doesn’t drive.

“On the average day, I do not have ID with me,” she says.

This wasn’t an average day.

She’d thought she needed an ID for her doctor’s appointment the afternoon before, so she had her passport in her backpack. Carter: 1, Secret Service: 1.

But it wasn’t over yet. An agent making small talk about the camp’s upcoming theatre show escorted her in, and all she had to do now was clear a bag check and pat-down. Now, in a tank-top and shorts, it wasn’t like she could’ve smuggled in much. That didn’t stop her from complicating things for herself though.

“My reaction to the guy saying, ‘Listen, I have to go through your bag, was ‘Just so you know, I have some weird s— in there,’” she says.

On an island of weird s—, this isn’t much of a surprise.

What was surprising, at least for the now-piqued agent, was what was actually in the bag: nothing bizarre or dangerous, just Monsters Inc. band-aids and several packets of gummy worms.

She was home free. After trials and tribulations and graveyard-sneaking, she was let through and finally delivered the lukewarm iced teas.

One of the island’s nicknames is “The Rock,” but D’Angelo has a different way of putting things: Martha’s Vineyard, where “weird people live their lives.”

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Part II: My Ex’s Mom

In a small town, you can’t just break up with someone. That’s not an option. You might agree not be with someone anymore, but that doesn’t mean you won’t see them. Football games, freezer aisles, bonfires—each is begging for that awkward post-split encounter. And the smaller the town, the higher the odds.

Bryan Linn ’17 is from Cook, Minnesota, population 550. When he broke up with his girlfriend, he faced that age old small-town question: How do you stay apart from someone in a place built on togetherness? Answer: You don’t.

You can’t avoid someone in Cook. Bryan says trips to the gas station—which should only take five minutes—are 30-minute affairs filled with gossip and pleasantries. Most businesses are family-owned, so people don’t really leave, and old feelings have a way of hanging around.

All of these forces were at work when, a week after Bryan and his girlfriend split, his friends gave him a call.

“My buddies came and picked me up and said, ‘Oh hey, we’re hanging out with so-and-so,’” Bryan says. So-and-so, as in his ex-girlfriend.

“I’m like, ‘Oh, that’s nice,’” he says.

Because sometimes, it’s not chance that reunites former couples; it’s their best friends. He sat in the back of his buddy’s truck, angry, and learned of the night’s plan: They were going to do karaoke, and they had to stop at So-and-so’s house first. At least Bryan knew this sort of reunion was coming.

“When you break up with somebody [in Cook]…it’s always like, ‘Okay we broke up, I’m really sorry this happened, we can still be friends,’” Bryan says, “then your buddies are still their buddies, so it’s awkward.”

But they weren’t just picking up So-and-so; they also had to chat with her parents. It’s only small-town courtesy, after all.

“Her parents loved me, so this sucked,” Bryan says.

Then they hit the road.

We were driving along the road, middle of winter, very bad conditions for driving,” Bryan says.

So what’d he do?

“I roll down the window, and I say, ‘Hey guys, watch this,” he says with a huge grin. He climbed out the window onto the truck’s roof rack, winter wind whipping past his face, So-and-so watching from the cab.

“My buddy rolls down the window and says, ‘Hey Brian, guess how fast we’re going!’—this is a one-way street, middle of winter, just had a snowstorm—‘80 miles per hour!’” Bryan says.

Law enforcement doesn’t exactly police Cook with an iron fist. This is a town where kids cut down whole trees for bonfires in the woods, where Bryan sometimes rode to school on the hood of his brother’s car, where a guy named Creepy Craig lived in someone’s treehouse for a week. Rooftop shenanigans weren’t going to get noticed.

What So-and-so thought—that wasn’t going to get noticed either.

“At that point, I gave no f—s what she thought,” Bryan says. “I was there, I’m having a good time with my buddies.”

They reached the karaoke bar. Apparently the plan all along was that So-and-so’s parents would join too. So they met up and chatted for a second time, giving way to a spectacular only-in-America, only-in-Cook, Minnesota moment.

“Later that night I ended karaoking with [So-and-so’s] mom,” Bryan says. “It was so funny.” It wasn’t just karaoke; it was meta-karaoke, the song of choice reflecting the whole crazy situation as it happened.

“[We sung] ‘Stacy’s Mom’ [by Bowling for Soup] but I changed the lyrics to ‘My ex’s mom,’” Brian says. “It was great.”

A packed karaoke bar in Cook means you know a lot of people there, and odds are, they know you too, and your relationship drama. They joined in.

“The rest of the bar, where everyone was pretty intoxicated, started singing along with me,” he says. “It was just great. I don’t know what [So-and-so’s] expression must’ve been.”

Whatever it was, they all didn’t seem to mind afterwards.

“On the way back, we’d stop and BS, have a cigarette or a cigar or whatever, all talk and BS,” Bryan says. “Everything was mutual and happy and fine.”

Because in a town so small that your furniture store rents videos, that you play multiple positions on the baseball team, that you can drive across it in 45 seconds, a breakup isn’t really a breakup. It just means you have a few funny stories to share with someone over a cigarette in the snow.