Leo paused. His frugal heart winced. He looked at the person behind him in line—an elderly woman named Mrs. Higgins, squinting at a flip phone held together by a rubber band.

Leo realized he’d stumbled into the best BOGO deal of all:

Leo didn't care about the fine print. He just saw two sleek, titanium devices. But as Sarah began the setup, Leo hit a snag. He was single. He lived alone. He didn't have anyone to give the second phone to. "Can I just... have both?" he asked.

Leo lived by a simple, if somewhat exhausting, rule: . He was the king of coupon clipping, the master of cash-back apps, and a professional waiter of "seasonal clearances." But his ultimate white whale was the "Buy One, Get One" (BOGO) iPhone deal.

The salesperson, a calm woman named Sarah, nodded. "Great deal. You just need to add a second line and stay on the Unlimited Platinum plan for 36 months."

Mrs. Higgins beamed. "Oh, dear! I could finally see my grandkids on the FaceTime!"

"Mrs. Higgins," Leo said, turning around. "Do you want a new iPhone? If you pay for your own cheap line, I’ll give you the phone for free."