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It Never Hurts to Ask

shiny new (used) cowboy boots

The Boots

While shopping at a trendy second-hand store last month I spied a nifty pair of burgundy cowboy boots that looked about my size.

I wasn’t in the market for boots that day, but these were pretty and I couldn’t resist trying them on.

They fit perfectly!

There was a price tag inside each boot. It was a little yellow one like you might see at a grocery store. Or maybe the Salvation Army? It said $25.

What a steal for genuine leather made-in-the-USA cowboy boots! How could I NOT buy them at that price?

However, there was a piece of tape on each sole on which someone had written “$58” with a marker.

This seemed like a more realistic price, and I suspected the store hadn’t noticed the price tags inside the boots when they priced them.

I wasn’t going to buy them for $58, because I didn’t have an urgent need for cowboy boots. But if I could get them for $25, it was a no-brainer.

I took the boots to the cash register where two young women were manning (womanning?) the counter.

“Excuse me, are these boots twenty-five dollars?” I asked, holding the boots so that they could see the price tag inside.

They examined them inside and out.

“No, they’re fifty-eight,” said one of them uncertainly.

“Oh,” I said. I started to mentally kiss the boots good-bye…

And then I thought, ‘What the hey? I’m allowed to ask, and they can always say no.’

So I asked.

“Um … Can I have them for twenty-five?”

The young women looked at each other, and after the briefest of pauses, they agreed.

“Yes, it says twenty-five on the inside, so we have to let you have them for twenty-five.”


Anatomy of the Ask

It’s true what they say: It never hurts to ask. But how one asks can mean the difference between a successful interaction and an unsuccessful one.

These are the “ask” rules I live by:

1. I always have a right to ask, but I don’t necessarily have a right to get.

Remembering this basic rule ensures that my attitude as I’m asking is one of humility and gratitude, rather than entitlement.

Asking in this spirit leaves room for the other party to decide how they really feel about giving me what I’m asking for.

In the example of the cowboy boots, the women themselves seemed to feel it was fair to charge the lower price inside the boots, after being asked to consider honoring it.

2. Ask someone who has the power to say Yes.

If you ask someone who has to go ask the boss, it’s easy for the boss to say no to the employee, leaving the employee no option but to pass the “No” on to you.

3. Trust the other person to say No if they need to.

I don’t have to be responsible for the financial well-being of a store that offers me a discount. The store takes care of its own finances by adding a healthy markup to its prices.

Similarly, if I ask Mike to give me the last bite of his taco, I trust him to say No if he doesn’t want to give it up. If he gives it to me and resents doing so, it’s not my fault.

4. Asking is a good way to practice healthy entitlement

You can ask for absolutely anything. Just because you’re not necessarily entitled to receive what you’re asking for, doesn’t mean it’s stupid, wrong or mean to ask.

  • You can ask the bus driver to let you off in front of your house.
  • You can ask a stranger for ten dollars.
  • You can ask your doctor, dentist or hairdresser for free samples (or a foot massage).
  • You can ask your gym to reduce the cost of your training sessions.
  • You can ask your city council to declare your birthday a municipal holiday.

Asking is free and, done politely, does no harm.

You’ll be surprised how often you get what you ask for — even if you think there’s no way you should!

Have you ever been surprised to get something you asked for?

About Tina Gilbertson

Tina Gilbertson is a psychotherapist, speaker and author based in Denver, Colorado. She specializes in supporting parents of estranged adult children through therapy, consulting, and ReconnectionClub.com, an online support and information hub for parents. The author of "Constructive Wallowing: How to Beat Bad Feelings by Letting Yourself Have Them" and the "Guide for Parents of Estranged Adult Children," Tina is often featured in the media as an expert on communication and relationships. Her blog on PsychologyToday.com is called "Constructive Wallowing."
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14 Responses to "It Never Hurts to Ask"

  • Debbie
    November 16, 2013 - 9:10 am Reply

    Growing up in NYC, we were weaned on negotiation, since it took this skill just to navigate the streets! I agree, respectful asking does no harm and you okay get a bargain to boot (pun intended!) By the way, I bought an authentic pair of cowboy boots for $25 too from the Bargain News – just my size, in black and I love them! We should go line dancing!

    • Tina Gilbertson
      November 16, 2013 - 3:00 pm Reply

      Yee-haw! That’s great to hear you got a bargain, too. You draw the line, I’ll dance on it … or isn’t that how it works?

      • Debbie
        November 16, 2013 - 3:02 pm Reply

        I’m not sure Tina! I live in CT. Not many line dancing locales around these parts!

    • Tina Gilbertson
      November 16, 2013 - 3:01 pm Reply

      [Beaming] Thank you! I didn’t know if the photo would do them justice. They’re pretty spiffy in person.

  • Miss Maura 9999 Charlotte, NC
    November 16, 2013 - 12:19 pm Reply

    I agree: if you don’t ask, the answer is always no. I admire your concept of phrasing it in such a way that you receive your desired result A.K.A. tact, not always my strong suit lol; I too grew up in New York City where directness was the norm. I’ve been learning other ways since living in the South these past 21 years.

  • Miss Maura 9999 Charlotte, NC
    November 16, 2013 - 12:29 pm Reply

    Just Googled to see who wrote one of my favorite quotes, “if you don’t ask, the answer is always no.” The author is Nora Roberts, who wrote this: “If you don’t go after what you want, you’ll never have it. If you don’t ask, the answer is always no. If you don’t step forward, you’re always in the same place.”

    • Tina Gilbertson
      November 16, 2013 - 3:06 pm Reply

      That’s pure gold, Miss Maura. A valuable addition to today’s post. A hearty thank-you for your contribution.

  • multnoma
    November 16, 2013 - 1:28 pm Reply

    Where I come from
    if you ask,
    the answer was always “you’re a bad person”

    Still learning to get over that.

    Thanks for the Nora Roberts quotes

  • multnoma
    November 16, 2013 - 1:32 pm Reply

    advice for Mike:
    a friend once told me:

    it’s ok for me to say ‘no’ simply because I don’t want to say ‘yes’

    • Tina Gilbertson
      November 16, 2013 - 2:11 pm Reply

      Good advice, Multnoma. Now that we’re adults, we can freely exercise our rights, both to ask, and to say No.

      I taught an assertiveness class yesterday and during a role play, someone simply and quietly said, “No.” We all took a moment to marvel at the sheer power of that word, all by itself — no posturing, shouting, attitude, or explanation. Just “No.”

      Actually, let’s not tell Mike about that. 😉

  • Blue Lemonade
    October 26, 2020 - 11:29 am Reply

    If you will never see the person again, sure, it doesn’t hurt to ask. Other than briefly appearing selfish and entitled to strangers, you have nothing to lose.

    But are there ever situations where it does hurt to ask? If you are (or hope to be) in any type of relationship with someone, you may damage your relationship with them by asking for what isn’t appropriate or deserved. An attitude of “it doesn’t hurt to ask” puts the other person in a position to be diligent with their boundaries so that they are not taken advantage of by your “healthy entitlement”. Saying that the other person “can always say no” is an excuse to shift the burden of keeping the relationship balanced completely on to the other person. You end up with a tense relationship, and likely a short one.

    • Tina Gilbertson
      October 28, 2020 - 5:55 pm Reply

      It’s tricky, Blue. Even with the gratitude and humility mentioned in the first point, there are people who have enough trouble with boundaries that saying no will be hard for them.

      I guess it comes down to the types of relationships you want in your life, and the “rules” you want to live by.

      Thanks for taking the time to leave a comment!

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