Tiger Woods
Tiger Woods, a golfing legend with a storied career and some public controversies, had a simpler high school life. His first love, Diana Parr, was a senior when he was a junior, and their first date was a modest dinner and a movie – nothing extravagant.

The high school sweethearts even attended prom together and captured this sweet photo. Diana wore a red velvet dress with spaghetti straps, while Tiger opted for a classic look with a black suit, white button-up shirt, and bow tie. Both sported wide smiles, reflecting their happiness at attending prom together in 1993, long before Tiger became a professional golfer embroiled in public drama and controversy.