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

Filed Under: Advice, Travel

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.


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.

Which philosophy do you operate under?

View Results

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?

  1. I hate to ask even when I know I am entitled to something.

    For example, if I am staying at Amex FHR rate eligible for free upgrade, I will take whatever I am given and will not ask.

    If I am not upgraded when entitled, even though there is availability, I will not argue, I will just make my conclusions about the property and will not likely to stay there again. But I will not agrue.

  2. I think your approach shows a lot of class. Hampton Inn hotels have a 100% satisfaction guarantee whereby you’re entitled to an unconditional full refund if you ask for it. I hope you’ll agree with me that no Hampton is ever 100% satisfactory, and I’m within my rights to have never paid for a stay at a Hampton. And yet I’ve paid for every one.

  3. While it certainly helps to know the rules and get the benefits you’re entitled to, I think that a kind word a sense of patience can go even further. There have been several times I have received that ‘last seat in First’ from a gate agent that appreciated a smile and a joke from me rather than a sense of ‘do you know who I am entitlement’ from an elite one tier above me.

  4. Also, I believe you should not have to remind or argue about perks or upgrades you are entitled to, they should come automatically without asking. For example, Amex Plat has dining perks in Canada. I used Amex concierge to reserve tables at restaurants under that program, and most restaurants provide perks automatically without asking, but one place (Coast Restaurant in Vancouver) promises a complimentary glass of champagne per person, but never delivers. I did not ask. I just stopped going there.

  5. I’m mostly like you. I’ll be persistent as hell when the rules are not being followed, but I’ll rarely ask for something I’m not entitled to.

    A couple of exceptions: I’ll ask for an early checkin or a late checkout when I need it, even when I know it’s not an entitlement, because it’s well established that it’s a reasonable thing to ask for. Also, when I get an upgrade offered spontaneously by the provider, but would prefer a different upgrade, I’ll ask for the substitution, but not complain if I’m turned down. For example, for some reason Avis at LAX loves to upgrade me to a Mustang, which I hate. I’ll go into the office and say “You’ve kindly upgraded me to a Mustang, but I really don’t want a muscle car. Can you give me something else? I’d love a Prius if you can give me one.” About one time out of five, I get a Prius. But I never go and *ask* for one if I haven’t already been given a different upgrade that I’d rather do without.

  6. I’ll ask for upgrades or refunds when what I’m given isn’t satisfactory, for example being assigned the last row in economy (where it’s noisy and the recline is limited) or when the company screws up on their part, like taking way too long to do something simple.

  7. I would never lie or look for a bs reason to get something from a hotel. But simply asking for say an upgraded room in a very polite manner is something I have no problem with. After all the hotel does the same when they have a pop up screen at booking asking if I would like an e-upgrade. I can say yes or no but am not offended by the pitch. There hey would you like to pay a little more if this suite is available at check in is the equivalent of me saying hey I am checking in do you happen to have a complimentary ugrade

  8. Perhaps it’s just the other side of the same coin, but I have asked “what the charge would be” for such-and-such. Sometimes I’ve paid the charge, sometimes not, and sometimes I’ve been provided with “it” at no charge just because I asked. I see this differently than just asking for a freebie outright. It shows a willingness to put skin in the game.

    It’s funny, all those “5 ways to guarantee an unearned upgrade to first class” kinds of lists tell readers to just ask. It infuriates me because I always feel bad for the great majority who choose not to be “squeaky wheels”.

  9. I only ask if I think there’s a fair certainty of receiving a ‘yes’ response. I would never ask for a free upgrade at an airport check-in counter because I know how and why they are allocated and I’m very low down the pecking order.
    That being said, I’ve been amazed at what I’ve received simply by asking nicely sometimes. You’ll get a significantly better response at a lounge counter trying to get an extra guest in if you are very polite instead of just demanding things like you own the place. A genuine ‘how is your day going today?’ is a good start – if they give you a genuine response like ‘its okay, had a pretty full-on morning but the afternoons are usually a lot easier’ you’re in for a much better chance of getting a favour than if they response ‘fine – how can I help?’

  10. Lucky, the reason you are that way is because you are German. Ve like to follow ze rules, zhey are not meant to be broken. I am the same way, living half time in Germany with my dad and half in America with my mom. When I am in America I feel slightly more inclined to say, ask for an upgrade, but in Chermany, I like to take what’s given and persist on what I’m entitled to.

    Just my thoughts,

  11. i only ever ask for two things, late check out and upgrade possibilities. the last word is key. usually i’ll just be polite and friendly as usual and then ask, “i was wondering if there are any possibilities for an upgrade”. in those cases it never hurts to ask and the benefit can be substantial. but i’d never fish for anything less or anything unreasonable.

  12. I’ve always believed that its okay to ask as long as you understand there’s a good chance you’re going be told ‘no,’ Staff know the rules and if they choose to bend them for you then why not?

    When traveling with my wife I’ll often ask at the hotel if any nicer rooms are available. Sometimes were told no, sometimes were offered an upgrade for an additional cost. Other times were given a nicer room for free. The hotel staff has every right to say no, but if they say yes, then great.

  13. I’ve asked for a later check-out or a room in a quieter area.

    I don’t ask for upgrades and certainly wouldn’t linger around the door of a lounge to ask someone if I can tag them in …… (contrary to what I saw recommended on another blog several months ago.)

  14. I know it’s hard to believe, but I try to be very nice to people who I interact with. I’ve brought dessert back for the late night desk clerk at my hotel because he mentioned how much he loved the baklava at the restaurant he suggested for us. I’ve traded a window seat with an inquisitive kid so that he could see outside for his first time on a plane. I think the world is more about the trade of goods and services. Sometimes it’s about doing something random and nice for someone (and if you’re a hotel manager or GA, sometimes that comes in the form of a upgrade). Every now and then, I run across a person who believes that too. Of course it’s not an every day occurrence, nor am I entitled to these random acts of awesomeness, but sometimes I’ll ask. If I’m turned down, I’m just as gracious and thankful than if they agreed to give me what I asked for. Roll the dice. Be nice. Continue to be nice if they say no and move on.

  15. depends how much energy i have, i prefer to do much of my negotiating online, like through the secure message center of bank websites,

    if a nice hotel employee asks me a simple question like, ” do you have any preference as to what floor your room is on” i usually take this opportunity to ask for an upgrade, like “well if you have any nicer rooms available then what i booked that would be great”

  16. I look at it as Travel Karma. When i travel for work, i usually dont ask for upgrades or anything, even if i am entitled to them. I know i am on an expense account, so if i dont get lounge access, not a big deal. And i will probably only be in my room for a few hours of sleep.
    If i am with my family for a vacation, then i will definitely make sure to receive what i am entitled to and even pour on some extra sugar in emails before i arrive trying to obtain the best accommodations.

  17. I’m an ask guy 🙂 thou I agree w/ Jason on Hampton Inns, I’ve stayed a lot never asked for refund.

    http://www.twitter.com/jp_antonucci I agree fully smile, witty, and appreciative plus being a tall white guy, I travel well

    True, Evan! only 1 birthday or anniversary per yer 😉 Ben has a good technique – obviously, lol!

    I thought the goal of our hobby is to travel well, on a dime, so to speak. I’m enjoying it as my limited time allows. Always enjoy reading others adventures and enjoyments. My next is JAL 1St SFO-HRD, so Ben’s recent trip report is very interesting and appreciated

    Enjoy, all, Safe landings,

  18. There is a fine line between not making a fuss and letting people walk all over you… if I lived my life like echino I will be getting no where. Although I must state that it is his prerogative. Now it depends, for something like a glass of champagne, I would do like what he did, if it was more like a starter or something or a discount 15% or more I would ask. Anything less is not worth my time. If I was supposed to get a room upgrade I’ll ask. So for me it really depends on what it is.

    Also I do not believe in letting people get away with taking advantage of me, so it rarely ever happens.

  19. I don’t ask for upgrades unless I’ve rejected all of the available rooms in my booked category. Which I have done in a couple of hotels.

  20. @Jay “Also I do not believe in letting people get away with taking advantage of me, so it rarely ever happens.”

    It sounds like something in particular prompted this comment. Care to share?

  21. @echino

    Hi enchio, having read your comments it seems like in some ways (despite not wanting or willing to argue) you are the most ‘challenging’ type of customer to deal with in a customer service industry because you are as you described…the customer who does not come back….without giving the service type the opportunity to redeem themselves.

    Please don’t misunderstand me, this is not a criticism of you as a person and you certainly aren’t obligated to provide a second chance nor should the onus on be on you to ensure that you receive what is promised or at least are eligible for.

    But for those of us coming from the customer service side of a situation, who are passionate about our jobs ‘winning an argument’ is really resolving an issue, especially when the customer or guest complaint has merit.

  22. Sure I ask for extra things. My requests are always reasonable, and I’m always gracious if they say no. As long as you are nice (and reasonable), there is no harm in asking for what you want.

  23. the only time i asked for anything was at a ticket counter of continental airline in sao paulo.
    the agent gal was so stunningly gorgeous and i asked her for her phone number.
    she politely refused and that was the end of my asking gig.

  24. Asking for a perk is not an issue unless there are other people in line waiting, which means someone in line may be late for something important. Also, a newer employee may not have the full training to search the computer system to accommodate your request. Being polite is nice when asking, taking no for an answer and being gracious about it shows true character.

  25. “It doesn’t hurt to ask” is literally true in most circumstances, I guess, but I don’t think that means one should do it. Directly asking for freebies or perks to which one isn’t entitled just seems sort of vulgar.

  26. The choice you provide for to vote do not mention the possibility I often find myself in: I am not sure of just what I may be entitle to, so I just ask. 🙂

  27. “I’ll ask for upgrades or refunds when what I’m given isn’t satisfactory, for example being assigned the last row in economy (where it’s noisy and the recline is limited)”

    That situation is hardly a reason to ask for an upgrade or a refund. That is just whining.

  28. I am exactly like Enchio and completely agree with Martina, people like us are frustratingly difficult to deal with. For us, you only get one chance, there is no opportunity to fix a situation for us. Not really good for us or the service provider.

  29. 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.

  30. 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

  31. 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.

  32. 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!

  33. 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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