Unlock the Surprising Secret Behind Remedial Tailgating That Could Revolutionize Your Recovery Routine!

Unlock the Surprising Secret Behind Remedial Tailgating That Could Revolutionize Your Recovery Routine!

Here I am, deep in the trenches of the college hunt—juggling two high school daughters, endless college fairs, and a flood of brochures from schools that, frankly, I barely recognize. It’s like Groundhog Day with a twist: ten campus tours, all bleeding into one another—stone facades, giant bookstores, cramped dorms—and by the end, we’re all whispering, “This feels like the one.” But here’s the kicker: I realized I’d been approaching this whole ordeal all wrong. What if picking a college wasn’t just about the kids? What if us parents could snag a second chance at those glory college days through our kids’ choices? Welcome to the “Do-Over” era—where your kid’s next school is as much about your missed experiences as their future. Sounds odd? Maybe. But paying for college already feels like draining your retirement, so why not indulge in a little nostalgia, sunburns and all? Intrigued? Dive in and discover how the modern college search is flipping the script for parents and kids alike. LEARN MORE

Estimated read time4 min read

Oh, I’m in it. I’m deep into the college-search process with my two high school daughters. College fairs. Arcane admissions data. Mailboxes stuffed with brochures from schools you’ve never heard of. We, as a family, have toured an even ten. They are starting to blend together. Lots of stonework . . . huge bookstores . . . minuscule dorm rooms. At the end of every tour, we look at one another and say, “This feels like it could be the one.” My own personal Groundhog Day.

It was when I started talking to friends who already have kids in college that I realized I was going about this all wrong. Among my generation, a new way to pick colleges has emerged. I call it the Do-Over.

Everybody wishes they could relive their college years. Well, you can. Not by going back to school yourself—that would include all the boring parts—but by steering your college-bound kids to what you miss (or failed to experience the first time around).

An example. A friend in often-frigid Chicago—none of my buddies would fess up to any of this under their real names, so we’ll call him “Carmy”—told me that he only considered warm-weather schools. “Nothing north of Tennessee. That was the rule,” Carmy said. The child went to Texas Christian University and the parents bought a bunch of clothes in Horned Frogs purple for their numerous weekend visits.

This article appeared in the September 2026 issue of Esquire
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Or consider “Jimmy.” He went to a small college in chilly Connecticut back in the ’90s. He sent his daughter to the University of Miami. During last fall’s epic run by the Hurricanes football team, he found himself flying down to attend no fewer than four home games. (And to see his daughter.) Jimmy doesn’t even like football! He was there for the tailgate. He comes back sunburned like John Candy in Summer Rental.

My friends aren’t alone. Two back-to-schools ago, The Wall Street Journal estimated that almost twice as many northerners were going to public schools in the South as in the early 2000s. But that story was about the kids. Go to an SEC tailgate. Go to almost any southern college that has a semblance of a football team: You will see dads in Hokas and sunburned faces. Moms in “cute boots” holding the seltzer of the moment. The kids are ripping it up, Mom and Dad close behind.

“Mike” and “Becky” sent their daughter to Ole Miss. Mike liked it so much he bought a condo in Oxford—before his daughter’s freshman year began. Now when he and the wife head south for a football game or Parents Weekends (yes, plural) and party like it’s 1992, they can simply walk back to the condo and crash. The old days, but with a 65-inch flat-screen and a Tempur-Pedic king-size. The Do-Over upgrade.

This may all sound like a bit much, but as long as you’re going to drain half your retirement account to pay for your kid’s college, why not get yourself a second shot? After all, that is the reality. Seventeen percent of families pull from retirement savings to afford college, and 34 percent drain other parental savings or investments. I balked at the tuition numbers, trying to square costs with majors’ employment rates and earning potential. Then I realized I was doing the math all wrong. My buddies compare $65,000 for tuition up north against $28,000 plus 77 degrees at a school down south. That math is easy.

To be fair, most families are genuinely trying to find the best educational fit for their kids. Lifestyle has just become a more important factor. That’s not crazy: The fact that education isn’t just about class is one of college’s greatest revelations, right? Which is another reason the bougie schools up north are getting challenged hard by the Red Solo Cup–and–Visor colleges down south.

My daughters see both sides. They show me Insta posts of the fun being had in Gainesville (University of Florida), Athens (University of Georgia), and Auburn (Auburn University). They also have eyes on schools up north. I asked one why. “The school has to feel like a home, but I don’t really care too much about the dorms and the buildings. It has to be a place that helps me get where I want to be with what I want to do.” Well said. I gave her the $20 of gas money she’d asked for.

I told a friend, on the other hand, that my daughter was looking at Providence and DePaul. His reaction, after thinking for a second: “They don’t have football, right?”

Is it possible that, after generations of parents had to convince recent high school grads who were wowed by the windfalls from their first full-time jobs that even more school is worth it . . . that something has flipped? That the kids now will have to be the adults in the room?

Not so fast.

One of my daughter’s friends was at the house the other week and told me he was going to Ole Miss. Curious what he’d study, I asked him, “What are you going there for?”

He looked at me funny. “I’m going for four years.”

So are his parents.

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