The 3 Pitfalls High School Sweethearts Face, and How We Overcame Them

I married my Homecoming date, Annie.

This despite the fact that I wore a sweater vest to the Homecoming dance and that we dated for 11 years before getting married. That’s right…11 years! That’s totally a record, and one that I might add, I came very close to not achieving.

Each year I get invited to speak at 20 to 30 universities across the country about my travels and my books, which are regularly selected as the common reading books that all incoming freshmen are supposed to read. And each year there is one question that freshmen women who are still with their high school boyfriends want me to answer:

“How did Annie put up with you?”

Only Annie can truly answer that question, but this is my attempt to hash out the three pitfalls that all high school sweet hearts must overcome to have a lasting relationship, and how we overcame them.

#1 High school guys are jerks

Annie lived right across the street from our high school. My 17-year-old peanut brain, couldn’t figure out why she couldn’t just walk herself over to the football field instead of having me pick her up for our first date to the Homecoming game. After all, I had just cleaned out the inside of my Trans-Am, and why would I want someone tracking dirt onto my freshly Armor-alled floor mats?

When I was 17, chivalry was dead. I killed it repeatedly.

I was on the homecoming court and I had to wear a suit. It was a cheap suit and my blond leg hairs poked through my black pants. We laughed. It was cold but our interlocked sweaty hands stayed warm for the entire game.

This is how our high school courtship went: Moments I’ll never forget interspersed among moments of me being a dope.

I like to think that, relatively speaking to other high school guys, I was a good boyfriend. Still, that’s grading on a pretty ugly curve. I ignored Annie in the halls. I barely acknowledged her presence in the company of any of my friends.

In turn, she treated me like I was a teen heartthrob. She wrote me poems. She had pictures of me hanging on her wall. She wore my jersey to basketball games.

Now that we’re on year seven of our marriage, and year 18 of our relationship, I’m not quite on the pedestal I once was. But pedestals easily topple. Those early laughs and those innocent quarters of handholding were building a solid foundation that would last.

High school guys are jerks, yet in high school, jerks often get the ladies.

For high school sweethearts to last, a guy needs to unjerkify before his lady’s intolerance for jerks wanes.

#2 The clock is ticking

The summer after I graduated high school, I broke up with Annie. I was moving on to college life, and college girls, and she still had two years of high school. At least that was my logic.

We spent hours that summer almost breaking up before a late night session of conversation and tears and I’m sorrys finally made the breakup official.

I was really bad at breaking up with Annie. I think that’s because I really liked her and didn’t even know why I was breaking up with her. It’s just what the older high school boyfriend was supposed to do before he went off to college.

We almost never fought. Our relationship wasn’t full of drama. We had a blast together. I was distracted by what was next. What would happen to us when I was traveling the world like Indiana Jones or sailing the seas on a sailboat, or some other daydreamer’s global quest that had nothing to do with any small town in the Midwest?

The breakup didn’t last very long. None of them did. And there were others. Annie graduated high school and went to a different college. I graduated college and did the six-month world backpacking trip thing before finally settling down as a SCUBA instructor in Key West.

If there were ever a job for a twenty-something year-old man to pickup women, it is working as SCUBA instructor. I once had one of my female students tell me my eyes were the same color as the blue ocean. I don’t mean to brag, but I had to dodge several advances through the years. It was easy to pass up on these opportunities to explore another relationship because I had Annie, who I simply couldn’t imagine living without, even while we lived thousands of miles apart.

Annie graduated college. By this time we had been dating for 6 years.

“What’s next?” There was that question again.

We moved together to North Carolina for a few years. I worked retail and wrote. Annie worked as a nanny. We were happy in our 600 square foot apartment except for one thing…

“What’s next?”

Annie wanted to move back to our hometown in Ohio.

The relationship clock doesn’t stop and it gets a really early start for high school sweethearts. By the time Annie had graduated college, we had dated for six years. By the time we moved back to the Midwest after our time in North Carolina, we had dated for eight years.

Everyone wanted to know when we were going to get married. They had been asking for years. And now Annie wanted to know if marriage was even on my radar.

It wasn’t.

The amount of time you are in a relationship increases the pressure to get married. When the clock starts for high school sweethearts they are further from the time in their lives where they will be emotionally and financially stable—at a place to be married.

According to a National Health Statistics report, couples who get married before they are the age of 20 only have a 54% chance of remaining married for ten years. The odds increase to 69% if a couple marries between 20-24, and to 78% if they get married after 27. (We got married when I was 28 and Annie was days away from 27.)

High school sweethearts are more likely to get married sooner, which means they have a higher chance of having a failed marriage.

The pressure to get married after dating for eight years was too much. Annie broke up with me. We didn’t talk for three months. I traveled to Central America tracking down where my T-shirt was made and she moved to Muncie.

I returned home early from my trip to attend the funeral of a boat captain I had worked with in Key West. Captain Ralph had always told me: “Marry that girl.”

I decided to take Ralph’s word’s to heart, and I got busy trying to convince Annie that there was a future for us.

Eventually I did marry that girl, and now that girl is the mother of my two awesome kids.

#3 You become different people

I had my Trans-Am phase. I had a time in my life in which I read too much Thoreau and Emerson and was a bit too transcendental to be sufferable for some folks. I had my Indiana Jones phase where I pushed the limits of adventure a little too much–too close to deadly venomous snakes, too deep beneath the ocean’s surface. And then, eventually, those things added up to be me.

My friend, author John Scalzi, wrote about this phenomenon years ago on the occasion of his 20th high school reunion:

I’ve often said to people that as far as high school reunions go, the 20th is the one that really matters. At earlier reunions people are still finding their way into the adult world, and at the later ones you find out which people have left the world entirely. At the 20th, however, everyone’s pretty much become who they were going to be. You’re irrevocably adults, you have spouses and children and status and you are you. This is one reason I was so keen on coming to this reunion: I wanted to see the people the people I had known as they were growing had become.

Annie went through different stages as well. She worked as a dolphin trainer and a nanny.  She crocheted a bit. We were lucky that at each of these stages we grew together—despite all of the above challenges—and not apart.

It’s like we were different people who fell in love all over again at each stage of our lives.


I’ve circled the globe multiple times reporting from 80 some countries before I finally realized that the girl of my dreams grew up only three miles down the road from me.

I’m lucky to have married my high school sweetheart, and I’m amazed as much as anyone else that she still puts up with me.


Stinger Contos says:

You Bastid! I’m sitting here with tears in my eyes…I was not prepared for that. Magnificent article, and I know because I have read so many bad ones. I remember a slightly older version of the Homecoming Guy, but I must admit you turned out OK, and that is a good thing, squeezed Ralph in there too, nice, very nice. Annie is a saint and I knew none of this, which for you was probably a good thing as far as your survival at Subtropic is concerned. A great read that evoked many emotions…as I stated at the start…You Bastid!

Much love, Brother.

You just ‘spent’ almost 1,500 words telling the story of a woman who spent over a decade of her life courting you…apparently more than you were courting her…that so far…is a testimony of marital bliss(?)…that typically…historically…is never justified as an appropriate claim until 2-3-4 decades of marriage have become the supposed ‘evidence’ of that…bliss(?)

I’m not trying to disclaim your relationship…but at this point, I think her most impressive resume bullet should be “Stamina”.

However, your words have elucidated for me…the challenge I now face because of this seed you have planted in my intellect…?

How in the hell will I verbalize the explanation…of why a woman…who waited till I was in my 60z/70z(?) before I was suddenly…now able to justify such an attempt to talk…a woman…into ‘sharing’ her life with me…with all the implications that implies…?

I’ve identified a candidate…but none of us should hold our breaths in anticipation.

btw…your words are an incredible testimony…but I hope I don’t have to tell an 11-year story of courtship…should I be tempted to…tell my story.

I had heard about Annie having to do the lion’s share of the wedding planning while you were off in Asia. I did not realize you were high school sweethearts. Many blessings and a long happy marriage to you both.

Beth says:

College sweethearts skip a FEW of those steps, but…..

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