Can you upgrade hotel room after checking in?

Can you upgrade your hotel room after checking in? Ugh, let me tell you, it's a crapshoot! I've tried, believe me. It feels like you're begging for scraps sometimes, you know? Like, I remember this one time in that little motel in Poughkeepsie – nothing fancy, right? – I asked if they had anything with a better view, and the guy behind the desk just shrugged. Said they were all booked. Which, fine. But I saw a whole bunch of empty rooms later that night! Made me wonder…

Honestly, politely asking at check-in might work, especially if it's a quieter hotel, maybe a Tuesday night in the middle of nowhere. But don't go in expecting fireworks, especially if you're not staying at a Ritz-Carlton or something. Even then, if it's a busy weekend, forget about it. They're not exactly handing out free upgrades like Halloween candy, are they? Five-star hotels, yeah, maybe if they're practically empty – but even then I've heard stories. My friend, Sarah, tried, swore she was super nice, and still got nothing. Said the manager practically looked her up and down!

So, what's my best advice? Honestly? Request the upgrade when you book. It's way, way more likely to work then. Think about it – they've got your credit card details already, they know you're committed, and it's less hassle for everyone involved. You get what you want, and they fill a room. It's a win-win! Much better odds than playing the post-check-in upgrade lottery, trust me on that one.