“It Can’t Hurt To Ask” When Traveling — True Or False?

By: Ben Schlappig

Published: February 16, 2015

34 comments

Obviously everyone approaches life differently, and there’s no place that’s more apparent than in the travel industry.

Perhaps contrary to how I sometimes come off on the blog, I’m generally pretty quiet and try to be cognizant of my surroundings. Many might say I take it to an extreme. I hate talking in elevators, because I don’t want to disrupt others, and I won’t even talk on my phone in an Uber without asking the driver. I realize I’m an extreme case, but stay with me here…

From observing how others travel, there’s one area where I’ve noticed an especially stark contrast.

When observing how others travel, I can’t help but notice something consistently that I can’t bring myself to do. There’s a common phrase that “it can’t hurt to ask.” It can’t hurt to ask for a room upgrade at a hotel, it can’t hurt to ask for an extra guest for lounge access, it can’t hurt to ask for a fee to be waived, etc. That’s a philosophy many people seem to live by, though personally it’s not something I can do.

W-Guangzhou-Hotel

I kind of take the opposite approach — I know exactly what the rules are, and I’ll be persistent as hell when it comes to making sure the rules are followed (for example, as a Starwood Platinum I’ll be persistent with room upgrades if there are still several suites for sale).

But under normal circumstances I can’t for the life of me bring myself to ask for something I’m not entitled to. And perhaps this is an area where ignorance is bliss. When you know exactly what you are and aren’t entitled to, it’s much tougher to just “fake dumb.”

Don’t get me wrong, maybe once or twice a year I get myself into a crappy situation where I do ask for an exception, like with the inaugural Etihad Airways A380 flight. But it kills me to do it, and I only do it when there’s an “emergency” situation.

So I’m curious to hear how you guys approach things when traveling.

[poll id=”48″]

Let me know which ideology you guys subscribe to! And if you subscribe to the “it can’t hurt to ask” ideology, what kind of success have you had with it?

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Michael Sitver Guest

February 21, 2015, 5:38 pm

My strategy is to "ask with an out". I never hesitate to ask, but unless it's a request that I seriously expect should be granted, I preface it with "I know the answer is probably no" or something a bit less direct, but similar in manner. I'm polite, and I make sure the employee recognizes that I would not be upset or surprised at the request not being granted. It works in a surprising number of cases.

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Cath Guest

February 17, 2015, 1:07 pm

I always know/follow the rules, 'cause - you know - "knowledge is power." Meanwhile, I married someone that is oblivious to/forgetful of said rules, so he's already asking an agent for an upgrade, etc., while I'm still arranging our bags or searching for a reservation confirmation in my purse. It's the best of both worlds!

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Sice Diamond

February 17, 2015, 11:19 am

I think for the casual traveler it's fine to ask; it's likely he/she doesn't know the rules at that location and it's also likely he/she is spending a lot on an infrequent vacation. No point in not asking. But for the more seasoned traveler it's less important since there's a good chance you're an elite and already get the perks.

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jfhscott Member

February 17, 2015, 10:18 am

Well, there must be some consideration of what one is requesting. A noon check out - def d/n hurt to ask. Reservations at a hotel's otherwise booked restaurant? OK A suite upgrade? no. First class upgrade? no. I suppose the question to ask is whether the request is reasonably in line with what one has paid for. And, Lucky, I note that you do not live by the it "does not hurt to ask rule", but after a while, if you were to do so on a busy travel schedule would be reduced to very taxing panhandling. I could never bring my self to it

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Jamie Guest

February 17, 2015, 7:37 am

I believe the statement, "It can't hurt to ask", but rarely do so. I tend to do it over email if I do want to try for an upgrade, because I feel awkward standing at the desk there. I also think that they allocate their rooms the day before and if they have a lot of empty rooms they will put the high status people in the nicer ones. Or as has happened to me before, if the hotel is completely booked, they will look to upgrade some with status, so that they can fit more people who want to pay only for a standard room. So, if there is something I particularly want (like a view of the arch in St Louis), I mention it in an email or in the comments of the reservation, but the vast majority of the time I take what I get.

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