Below are two simple examples of "it doesn't hurt to ask".
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I did the whole smart couponing thing and used "sign up to save" discounts on every site I could, googled "promo code for x" for every other site, and took advantage of sales or clearances they had running on the sites. Other than a deal I bought on Groupon which was a huge disappointment in my opinion, I was pretty proud of what I had bought and what I had saved.
Then; Black Friday.
I had bought a couple things on the Red Thursday from some online US retailers. I thought I was doing pretty good with coupon codes and free site wide shipping. Then Black Friday weekend came and both sites announced better deals than I had bought my items for. Of. Course.
This is a lesson in, not beating yourself up for missing an even better sale, but instead being willing to ask. I always say it doesn't hurt to ask.
So I emailed both companies. Said that I either needed to do a) cancel the order immediately to attempt to re-buy the items over the weekend, or b) have them simply credit me the difference instead of potentially losing the sale. I explained the date I had bought the items and the discount I expected to be applied to my credit card (on one site it was $10 and on the other site it was $12). I fully expected the response to be "tough shit" or "snooze ya lose", but I went by my own advice and sent the emails, plus a follow up email to both on Sunday.
In the end, Both companies did refund me the amount I had asked on the Monday. $10 might not be a lot of money, but $10 US can buy a couple more gifts up here, and I'd rather it in my pocket. I profusely thanked both companies and told them they would have repeat business from me.
So, shameless plug to some of the greatest sweatpants ever Crotchgear and to a necklace for every person in your life, The Needed Necklace.
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Another example was for this magazine subscription we get, which recently got taken over. We had issues at the takeover, as suddenly a couple of the magazines my grandma loves to read dropped off their subscription list and she no longer got them.
We called in and emailed and complained, needing an explanation, citing how unhappy we were with what we felt like was an almost bait-and-switch as we didn't get an email notification saying any magazines were going to disappear, in advance of the next monthly payment (which I explained I would have cancelled the subscription for had we been notified).
Apologies and fluff later, they offered me 3 months at half price. That took me into this month, December, paying something like $7 for 112+ magazines.
At work, we had a company come in to pitch something to us, and brought us "gifts" (bribes?) which included a free 3 month subscription to this company.
Well I started scheming how I would cancel my subscription, then re-buy it (under a different email) at the current holiday promotional discount of 60 days free, then would cancel that and buy it again (under a new email again) with the bribe gift of 3 months free. In my brain it was all working but I was exhausted thinking about having to remember all these dates.
But, I decided to call their customer service again to see what could be done. Could they just credit me these months instead of me jumping it around? Could they just apply this three month discount to my existing account?
The answer to both was yes, in part. They offered me a 50% discount for the next three months, and advised that my three month promotional coupon could be applied directly to my account when I wanted it to be. Saves me the hassle and sounds good to me to save some more money!
