How to find discounts that shouldn't exist (without being a shameless mooch) Part 2: HOW to ask

Including word-for-word scripts for that inevitable rump-pucker

Welcome to Imperfect Working Order—where we survive capitalism while sick and do it as fancily as possible, running microbusinesses, smooching hotties (well, one hottie, currently), and rolling with MEeps and regular peeps alike.

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Last week, we covered WHO to ask for magic secret discounts that no one will tell you about. Why? Because illness is expensive (times twelve) and we need all the magic secret hidden discounts we can find.

We learned: you have to ask. And having to ask kinda sucks, if you’re picturing what I think you’re picturing:

You, in a worn (but clean) babushka scarf, puppy-dog-eyes pleading in supplication toward whomstever might grant you thirteen cents off an elderly potato.

Yeah, we’re not doing that. (Although you would look fire in a bubushka scarf.) Asking for discounts is, in fact, NOT going to suck. It’s going to rock. At least it did for the commenter on the last post who saved $4,000 on one transaction.

So go read Part 1 to make sure you’re asking the right places, as that’s the biggest lift. Then, upgrade that scarf with some main character sunglasses and allergen-friendly lipstick and let’s sashay off to save.

Obviously me, on my way to ask for a discount like a ~lady~. Photo: Lance Reis

The second rule of artful discounting is to ask with class.

This isn’t shameful—plenty of people who have plenty of money ask for discounts. (Praise me for not inserting a political crack here. It took the entirety of my willpower.)

There’s no need to simper, whimper, or beg—just ask.

Straight up, with self-respect, politeness, curiosity, and absolutely no expectations.

It’s just a question. In many cases, it’s a request for information, nothing more.

You don’t need a sob story. Over-explaining raises suspicion, not goodwill.

You’re going to be nervous the first few times you ask. That’s okay. Later, you’ll be breezily slipping this life-changing question into cash-register convos and customer service chatskis.

Scripts to use:

At a busy checkout before the total rings in:

“I just wondered if I qualified for any discounts?” (This does sometimes get you a store credit card offer—pass.)

On a customer service chat:

“Is there any way you could help me save more on this bill?” (Customer service workers are there to help! Magically, my car insurance reduced.)

Emailing a company before you buy:

“I’d really love to try your product. Do you have any discount codes or specials coming up?” (A microbiome test company kindly gave me a 20% off code just for asking.)

Talking to the hospital financial department:

“I’ve heard there are assistance programs and discounts. Could we discuss options for my bill, please?” (As I said in Part 1, one of my greatest life regrets is not finding out I qualified for FULL forgiveness for years on a modest salary, after it was too late.)

Finesse the query:

I personally think it’s fine to mention the D word (disabled), briefly, if for no other reason than it sometimes gives them a specific code on their machine to push.

This shouldn’t have to be said, but it’s something I needed to hear at one time, so: announcing you’re disabled isn’t sharing a sob story. It’s just a fact—a shorthand that says you’ve probably suffered severe economic consequences.

Never, ever say, “I’m so sorry to ask.” If you’re asking the right people, you shouldn’t be sorry. Assume they have programs and policies in place, and you’re just curious.

Accept with grace:

If a discount is extended, thank them for both the discount and for having the discount program in the first place. I personally do not haggle. (Exception: anyone who is genuinely trying to rip you off. Case in point: insurance companies. Did I once fight my way from a $3k totaled car claim to one over $8k? You bet your sweet rump I did.)

If it’s a no, cool! Thank them for looking into it or letting you know.

If it’s a poorly run megacorp, you might land in an endless loop of customer service transfers. If you’re remotely considering cancelling (and maybe you should if their service is this awful), drop the word “cancel.” This often gets you to a “customer retention” program (aka…discounts). You can always change your mind on canceling (or just hang up during the hold music if it’s getting too ridiculous).

I asked for a discount on this (slightly stained) secondhand jacket that I wear every jackety day of the summer. Store-Owner-Dude said no. I bought it anyway…and he tacked on a pair of shorts for free. (Link to trike below.)

The third rule of artful discounting is to lead ALL your consumer transactions with extra kindness.

Whenever possible, be an extra kind customer—period, not just for discounts. Especially at the corporate level, many customer service agents become dehumanized receptacles for customer rage. A little kindness goes a LONG way.

I *always* start the customer service chat with a “thank you”: “thanks so much for taking my call” or “thanks a bunch for your help today.” It’s an easy way to put everybody in a Midwestern friendly-fest from the start.

It’s not the point, but sometimes you’ll receive a discount just for not being an arsehole. Which is sad, but until arseholes get charged more, take it!

I didn’t ask for this discount (thus breaking the first rule of artful discounting!)…but just being not a dipwad of a customer netted me $5 while I worked out a return for damaged product at Target.

Recently, I struggled to make a gift card work at my local coffeeshop for three weeks…patiently, politely, unbothered. They wound up giving me ANOTHER (working!) gift card pre-loaded with extra funds and thanked me for not being an entitled bovine.

The fourth (and final) rule of artful discounting is to always be asking.

If you only ask every once in awhile, that’s fine…but it makes it harder to find the super secret discounts. You just forget. You get sweaty when you do remember. It never feels comfortable and you spend money you shouldn’t have to.

When you ask the right places all the time, you find more discounts (obvi). That gives you the motivation to keep asking. Then the asking gets easier. Aaaaaask. Just do it. The first time is hard; the thirtieth isn’t. Future you is going to appreciate the living crap out of current you.

In fact, let’s just do one now together. 5 minutes, max. If you’ve got anything left in the tank, pick one of the following:

1. Call your biggest medical bill (dentist, labwork, PT, whatever) and politely ask what the options are for making it more reasonable

2. Send an email to the next specialty product you need (functional medicine test, mobility aid, wearable) seeing if they have any discount codes for your situation

3. Hop on a live chat with a monthly bill provider (internet, car insurance, streaming service, software subscription) and see how they can lower your bill

Please let me know how you did in the comments! I knocked $3 off my evil internet…which seemed pretty underwhelming, so I sacked up and asked a neighbor to split it with me. We’ll totally fudge that and call that ~$45 off a month and ~$550 a year, why the heck not?

Finally…

I’m sorry you have to do this. It’s a pain in the toochus. (Is that how you spell toochus? IDK.) But it’s also one of our most powerful tools for staying afloat. It adds up, especially on medical bills.

So adjust your most trustfundy scarf, don thy sunnies, and hang onto your paper—with chin held high. (As high as spinal degeneration, fusions, or migraines allow!)

Speaking of discounts…here’s a few you don’t have to ask for.

I only recommend stuff I LOVE and use myself.

• Get $100 when you open a new Ally account using this link. (Gives me $50, too.) Minimum deposit is $1k. I’m so mad no one told me about high yield savings until I was nearly 40. (One reader said it worked on desktop, not on phone…heads up!)

• Get a $200 bonus (and then up to 3% cash back forever) on a no-fee card with American Express with this link. (I get $75.) Hot tip: go through their “special offers” to really load up on cash backs. I use Amex for both business and personal.

• Take $60 off a Liberty Trike like mine with this link (I think it gives me $60, too?) For the cheapest deal, get the “Classic” (aka, old, aka, mine) model or a refurb.

• If you feel a stirring to support this work, you can Venmo my “parent company” @flyingbicycle or fulfill my wildest n95 mask dreams on MyRegistry (my b-day was Wednesday!). Big time gratitude in advance.