The cheesy line that scored my friend hotel room upgrades, rental car deals
It is one of my favorite stories in my book, and it is still working for my friend today
Hi there, my friend.
In writing “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life,” I did more than 100 interviews, and it was one of the most enjoyable experiences of my life.
A huge part of what made these interviews so enjoyable was hearing people share stories of the successes they and their loved ones had in life. Some were big, some were small, but they all mattered.
One of my favorite stories in the book came courtesy of my friend, digital content strategist Christine Burke. (By the way, this is a different Christine than the one who told me how she saved $3,500 in this post.) It’s about a fun, sweet line that her late father would use to try to get upgrades at hotels and that Christine now uses herself.
[Christine] always asks for upgrades when staying at a hotel. She starts the conversation with a line from her father, Arthur McDevitt.
“He’d say, ‘Do you want to be a hero today? He used to say something like, ‘You can be a hero today if you help me, and then you can spend the rest of the day telling people you’re a hero.” She estimates that the line worked for her dad “about 50 percent of the time.” Now she uses it herself.
If that sounds too cheesy for you, that’s OK. Yes, it’s a little over-the-top, but it’s also a friendly, fun icebreaker. Say it to a hotel clerk with a genuine smile, and you may get an eye roll from time to time, but it can kickstart a conversation. Most importantly, it playfully makes your request not all about you. People are more likely to go out of their way to help if they stand to gain something.
With this tongue-in-cheek line, you’re giving people something positive, which they weren’t expecting, in return for helping you. It won’t work every time, but even if it doesn’t, you’ve given the person behind the desk something to smile about during a long shift.
This week, Christine told me that she recently used the line to get a discount at the rental car counter in Phoenix this past January:
In a direct message, she said, “We reserved a car with Budget, and the line was legit 2 hours long. I left [my husband] in line, dashed over to Alamo, and used ‘the line.’ Not only did she have a car for me, it was $200 cheaper. We were on the road in 20 minutes.”
“The woman at the counter was named Ariana… she chose heroism that day.”
I love this approach for so many reasons, not the least of which is that it works. I love that it is so simple. I love that it has a little fun with the idea of making a negotiation a win-win — people are more likely to help you if they get something out of it themselves, right? I also love that it could genuinely bring a smile to the face of the person behind the counter who has probably been yelled at a time or two that day.
But I think the reason why I like it most is that it reminds me of my dad. He was a huge inspiration for my book and for Ask, Save, Earn, and I’ve written about him a lot here, including this post:
I don’t think my dad ever did exactly what Christine’s dad did, but he TOTALLY would have. As I wrote in the post above, my dad never met a stranger. He could talk to anyone and loved to make people laugh. He was also an amazing negotiator, having spent three decades doing it for a living at State Farm Insurance.
This was about as up his alley as it could be. I wish I’d gotten the chance to share the story with him.
Would you ever try something like this? Or maybe you have your own approach? I’d love to hear about. Tell us in the comments.
More travel tips
I devoted a whole section of my book to travel, and it is a frequent topic here at Ask, Save, Earn as well. Here are a few travel-related posts from the past year or two:
And finally… The Not-So-New-Anymore-Year Challenge
I started the new year at Ask, Save, Earn by issuing you and my other subscribers a simple challenge:
“Sometime in January, contact a business you work with and ask them to change something.”
That’s it!
I called it The Ask Questions 2026 Challenge. You can learn more about it here…
Did you do it? If not, would you consider doing it now? It doesn’t take much time and can save you real money.
If you did do it, tell me how it went. There’s not much I love more than hearing people’s success stories of paying less, earning more or keeping more of their hard-earned money by asking the right questions.
Until next time!
Matt