There comes a time in every life when a choice must be made. Choose love or money. Eschew sentimentality or discard practicality. Pick either the University of Pennsylvania or Texas in the first round of the NCAA Tournament. Or West Virginia or Iowa in the second round.

For many with strong allegiances, it's a dilemma that pops up every year during March Madness: Do you pick your favorite school to advance beyond its likely point of elimination, or do you throw emotion overboard in pursuit of cash?

Marvin Fein, a law professor at the University of Pittsburgh, is a man who knows the quandary inside and out. The 67-year-old has followed college basketball for decades -- long before the days of bracketology experts and long selection show specials.

He remembers one night in the early 1960s when he and a buddy drove around the South Hills looking for a bar with an antenna big enough to pull in West Virginia television stations. It was the only way to see the Ohio State-Cincinnati national championship game, which wasn't being televised locally.

He's often had the opportunity to follow Penn, his alma mater, in the tournament, but rarely had the chance to follow them very far. In the last 25 years, the Quakers have made 11 tournament appearances -- and won exactly one game.

"I'm lucky enough to go to the school that goes to the NCAA Tournament every year," he said. "But I'm also unlucky enough to go to one that loses in the first round every year."

Still, Mr. Fein will often pick the Quakers to win their first round game. This year, they are a 15th seed, playing No. 2 seed Texas -- in Dallas. "That would be an awfully dumb pick to make," he said. "I may still make it."

Letting the heart control the brackets is a charming thought, but an utterly foolhardy one for Marty Spicer, an applications developer for Mellon Bank. A Morgantown native, he will pick against his beloved West Virginia Mountaineers -- or for his hated Duke Blue Devils -- if he thinks that's the ticket to victory.

It's a method that Mr. Spicer, 45, has followed for the more than three decades that he's filled out brackets. He also puts sentimentality aside in his other fantasy sports leagues, which have included baseball, hockey, football, NASCAR and even the Winter Olympics.

"Money outweighs loyalties, I'll be honest," he said.

Sure, he thought about picking the Mountaineers to go to the Elite Eight this year. After all, they lost to Texas by only one point when the two teams played in November.

"But Texas has gotten stronger and West Virginia has gotten weaker," he said, rationalizing the pick to himself. "I can't pick West Virginia. I gotta go for the money."

It's the kind of heartrending choice that Dan Pauletich prefers not to make. So the 36-year-old consultant has developed a system, and a rather elaborate one at that, to allow for brackets that appease multiple desires.

Every year, he does four -- no more, no less. His first is the "like-to-see" bracket, where his favorite teams get to upset and advance. Since his alma mater, Penn State, isn't in the tournament this year, he has Pitt going to the Final Four.

It's worth noting that even in the "like-to-see" bracket, the Panthers don't go all they way. "There is a point where reality takes over," he said.

He also does a "chalk" bracket, where he follows the seeds; a "knowledge" bracket, where he applies his best research; and a "knowledge backup" bracket, where he changes about six picks that were close calls in the first "knowledge" bracket.

This way, he can have Pitt going to the Final Four one one bracket sheet, but losing to Kent State in the first round in another.

In a sense, he's having it both ways. But maybe that's not so unusual in the love-or-money story lines that have spanned from Shakespeare to "Spider-Man 2."

Sometimes penniless Peter Parker ends up to be Spider-Man, or your sentimental pick ends up to be the University of Richmond Spiders, who over the past 15 years have won first-round NCAA tournament games as both a No. 15 seed and a No. 14 seed.

And sometimes, those who pick with their hearts win big. Last year's winner of $10,000 in the ESPN.com Men's Tournament Challenge was a senior at Michigan State who picked the No. 5-seeded Spartans to make the Final Four.

Even Mr. Fein's perennially overmatched Quakers made the Final Four in 1979.

A little sentiment never hurts, said Mr. Fein.

"You want to root for the teams you like, and also have them on your brackets," he said. "We're talking about basketball games that nobody has any control over."