I’d like to warn people about the potential dangers of studying history. I’m talking worse than paper cuts and eyestrain. We are shaped more than we realize by the past—events that happened long before we were even twinkles in our parents’ eyes. Once you start thinking about how things got to be the way they are, it’s hard to know where to stop.

Countless tiny events accumulated to create the world around us: what we say and do and eat and believe. Somewhere, sometime, somebody wore the first-ever pair of pants. It took years to determine that eating lobsters makes you fancy and eating worms makes your fifth grade classmates freak out. Things develop, slowly but surely.

In small communities, you run into people with long memories. They know how certain things came to be—or can at least make up pretty convincing reasons. History remains a part of the present experience. Of course, you find this in cities as well, but with the constant shifting of characters it can be harder to hold onto that shared past.

I wondered about that when I moved to Swan’s Island. A lot of people who live here have been around each other since birth. How do you live with so much accumulated history? How do you distinguish the person giving you tax advice from the kid who threw up in your parents’ backseat 40 years ago?

All of those stories and connections layer up and form the backdrop of daily life. You look at a new store and remember the school that was there. The vacant lot still reminds you of the playground where you broke your wrist in a game of tag.

I can see how it could be tough to get along with everyone in a place like Swan’s Island—hard to escape from a reputation. Imagine living in a community where at age 70 you still have to deal with the nickname you earned in middle school.

We all have periods we’d rather people forgot, but that’s the price you pay for keeping the good memories. And after all, when it comes to long memories, Swan’s Island has nothing on some other parts of the world.

I spent the summer of 2009 living on the western coast of Scotland. I had a scholarship to work on family farms and “research local traditions,” which meant I could go to dances, read wonderful folk tales, wander and chat with strangers.

I first arrived in the eastern part of Scotland, closer to England in distance and culture. When people heard where I was going, a few of them warned me about the West. “Watch out for people in the Highlands,” I was told. “They’re weird, religious, and make eye contact with strangers.”

It was probably the best preparation for Swan’s Island that I could get. If I bumped into an old woman on a walk, within a few minutes we’d have covered my marital status, home life growing up and the professional standing of the family I was staying with. One lady brought me along to a church service conducted entirely in Scots Gaelic—complete with bagpipes. I was in heaven.

The old timers I ran into sure knew their history. I spent a month on the Isle of Mull, a beautiful granite hill and peat covered island dotted with the remains of abandoned stone villages and churches. Many tenants were forced from their homes in the Clearances, a period when the large landowners, or “lairds,” realized sheep were more profitable than small family farms.

Prior to that the population dropped when the island’s young men followed their clans to the Battle of Culloden during the Jacobite Rising. I was warned to watch out for the Campbells—back then they’d fought on the wrong side.

I should just point out that the Battle of Culloden took place in 1746. To get a little perspective, that’s a full three decades before the American Revolution. Being warned about the Campbells is roughly equivalent to an American saying, “Gosh, I’d love to go bowling with you but I heard your family members were Loyalists.”

Of course, people had a sense of humor about it. But it’s fascinating how active a presence the past had in daily consciousness.

The active presence of history doesn’t always divide us into factions. It is often the foundation of our identity and everything that makes a place important to us. Life on a Maine island is not always easy. There are more convenient places to live if you want a nice view and access to fishing grounds. We stay here for the people, the memories, the stories. Whether or not we realize it, we stay for the history.

That being said, there is one lesson I’ve learned on the island that I think it’s my duty to pass on: don’t date a historian unless you’re prepared for the consequences

My fellowship advisor, town clerk and pal Gwen May is the source of this lesson. She’s lived on Swan’s Island her whole life apart from a stint on Matinicus. In her teenage years, Gwen had a cute ponytail and a fun-loving spirit. Like many kids, Gwen found true love a couple times before she was old enough to get a drivers license.

At 12, she was “engaged” to Normie Burns, famous (though perhaps not at that age) for his resemblance to Elvis. He gave Gwen a 25-cent diamond ring and had his mother in tears before someone pointed out to her that the kids probably weren’t going to go through with it.

By age 15 Gwen had moved on. Her beau then was Lawrence “Cappy” Carter, who came to the island in his early teens. They dated for a couple years on and off, “Mostly on,” Gwen told me. “He was a romantic,” she said, remembering the love letters he sent her while he spent time in Florida. Some included snapshots of him leaning on cars, playing the guitar, and grinning. “So I could drool,” Gwen laughed.

It was not meant to be. The couple parted ways, though they kept in touch in later years and are now old pals. Cappy lives in Ellsworth and occasionally visits the island.

Gwen and Cappy were recently reminiscing about the old days when Gwen, who always loves a good laugh, brought up the time that Cappy dumped her. Cappy denied everything—he was sure he never did such a thing. He had been in love!

Gwen May, historian to the core, went to her attic and brought out the fat envelope labeled “Cappy’s Junk” that had remained with her since age 15. She sifted through the letters (there were about 50 in all) until she found The One—the Dear John letter that ended it all. It was still in its envelope, stamped 1963.

Always ready to make a sacrifice in the name of history, Gwen let me scan the letter to add to our historical collection along with a photograph of the ring Cappy gave her. It was a worn circle with three hearts and the message “Going Steady.”

The letter itself was fantastic. Anyone who has ever been dumped will shudder at the opening lines: “Dear Gwen, This is the letter that I owe you. It is, without a doubt, the most difficult letter that I have ever written.”

Cappy goes on to explain that he has unexpectedly started to “like another girl very much,” and since he promised to never go out with anyone else as long as he and Gwen were going steady, he needed to make a clean break. The letter was sweet and thoughtful enough that he didn’t even give her the comfort of being able to hate his guts. Poor Gwen!

She got some small revenge, though, when she could produce the letter almost five decades later. Gwen described Cappy’s reaction. “He said, ‘At least I let you know before I started dating another girl,'” Gwen laughed. “Yeah, right.”

There’s nothing like documentary evidence to gain a point, and solidify an old friendship.

Perhaps island life is a good treatment for heartache. Nothing takes the drama out of a relationship like seeing the other party on a weekly basis, buying milk and mowing their lawn and driving to work. With so many tangled webs, at a certain point you end up just letting go.

Maybe that’s the origin of the wonderful sense of humor I’ve found out here. When your ex-girlfriend of fifty years hands you the original copy of your breakup letter, what can you do but laugh? It might be the only cure for history.

Editor’s note: This week, Kaitlin Webber ends her time on Swan’s Island as an Island Fellow. She tells us that her “There was a time…” columns will be compiled and published in book form in the spring of 2014. Stay tuned for more from this talented writer and perceptive observer of the past and present. We are grateful to Kaitlin for the wonderful stories she’s shared with readers.