Yes, you can certainly ask for an upgrade on United Airlines, but in 2026, the process is highly systematized rather than based on charm at the counter. The most effective way is to use the United app or website under "Manage Trip" to check for "MileagePlus Upgrade Awards" or "PlusPoints" opportunities. You can also ask a gate agent or check-in agent about "Day of Departure" upgrades, which are sometimes offered for a discounted cash price if seats in United First or United Polaris are still available. For Premier elite members, "Complimentary Premier Upgrades" (CPU) are automatically requested on eligible domestic and regional routes, though these are granted in a specific priority order based on status level and fare class. It is rarely successful to ask for a "free" upgrade simply because you are on a honeymoon or dressed well, as the upgrade standby list is strictly managed by the airline's automated system. However, inquiring politely at the gate about the current status of the upgrade list or available buy-up options is a standard practice for many seasoned United travelers.