Jackson Judd knew months before he asked his date to prom that his invitation was going to be over-the-top -- literally.
The senior at Mary Institute Country Day School earned his pilot's license when he was 17 and had set sky-high expectations the previous year: He'd taken his girlfriend, Abby Desai, to fly with him last spring and had her read the flight checklist aloud.
Judd had inserted "Will you go to prom with me?" as one of the instructions.
"The promposal has turned into such a big deal," he said. "There's totally a one-upsmanship."
After that first successful run, Judd took note of which promposals his girlfriend admired on Instagram. She seemed to appreciate one in which a boy had spelled out "prom" in lights on his date's front lawn.
He got the idea of spelling out "Prom?" on a field and flying over it with her.
The simple idea required some complex planning.
First, he looked up sizing for plastic sheeting he could use to make the message. Then he figured out how much he would need to create the display by drawing a grid. He bought 600 feet of black plastic sheeting from Home Depot and cut the strips in his basement.
He found a friend who had a family farm near Hermann, Mo., about 75 miles from St. Louis. Judd checked the forecast for two clear days, and drove out to the field to set it up. He held the plastic sheeting in place with firewood from the farm. The four letters and a question mark covered an area about the size of a football field. It would be visible from 4,000 feet in the air.
Desai didn't suspect a thing when Judd asked her to go flying with him two weeks before the big dance. They headed west, and for 15 minutes, Judd flew around trying to figure out exactly where he had laid out the tarp. He finally found the right field, tilted the plane wing down and flew by it for Desai to see.
"I was shocked," Desai said. "I never expected something so huge ... I was amazed he would make that much effort. I was over-the-moon happy."
Mission accomplished, Judd.
"I know I beat my personal best," he said, "but I wouldn't say I'm the king of promposals."
The couple, who have been dating for a year and a half, attended their prom earlier this month, and both reported having a fabulous time.
The first thing Desai's father said when he heard about Judd's promposal was: "Is your marriage proposal going to seem really lame compared to prom?"
The generation that has popularized a new tradition of asking a prom date in a big way -- and, of course, sharing that experience through social media -- may not hear another proposal for at least a decade after.
The median age for a first marriage has risen by six years during the past two generations. Nearly 60 percent of adults ages 18 to 29 were married in 1960. Now, it's 20 percent in that age group. The process of finding that life partner has also evolved for a sizable number of young people.
For millenials, dating, in its traditional sense, hardly exists. Interested singles are more likely to hang out than dress up and go on a dinner date. There are growing doubts in this cohort about monogamy. While fewer teens are sexually active now than in the '80s, the ones who are active are more likely to experience a fluid, hook-up culture.
Yet the vast majority of college students report a desire to get married one day. The Pinterest popularity of anything wedding-related remains strong.
So, if the fantasy still exists but the reality seems unlikely in the near future, why not create a bridge? Many modern prom rituals, from the professional photographer to the designer dress, resemble a wedding day. Costs and expectations keep escalating.
Some may criticize the promposal as a yet another narcissistic display by a generation that constantly needs to broadcast and be reassured that they are special.
But the promposal may also tap into another impulse: It may be a grand, romantic gesture by a generation holding on to a bit of innocence about what it means to be a loved in a commitment-phobic era. Even if there is an element of competition, going to the trouble to plan and execute a sweet surprise for someone is thoughtful and memorable.
It's useful to bear in mind, however, that no one should want the best night of their life to unfold in high school.
Kind of a bummer for the next 60 years if it was.
CAPTION 01: Jackson Judd created a football field-sized "promposal" for girlfriend Abby Desai.