While the romanticized idea of "asking for an upgrade" still exists, the reality in 2026 is that free "operational" upgrades are extremely rare just by asking. Airlines now use sophisticated algorithms to sell last-minute upgrades at a discount or award them automatically to elite-tier frequent flyers based on a strict hierarchy. Simply being "well-dressed" or "polite" is no longer enough to bypass these automated systems. However, it never hurts to politely ask if there are "buy-up" opportunities at check-in; sometimes, you can snag a First Class seat for a fraction of the original price if the cabin isn't full. The only times a gate agent might move you for free is in rare "operational" situations, such as if the Economy cabin is oversold but First Class has seats, or if your seat is physically broken. In these cases, agents look for solo travelers with frequent flyer status first. Asking won't hurt, but you should manage your expectations and be prepared to pay or use miles.