8 Splurges I Regret

I pride myself on being a penny-pincher, so when I choose to go big and spend mucho bucks on something, the experience instantly becomes more memorable.

Which sucks if it turns out to be a bad experience, like these eight splurges I’ve come to regret:

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1. My 40th Birthday Dinner

Approx. cost: $800 (reduced from $1,400)

I’ll begin with my biggest doozy. I spent the night before my 40th birthday at a Michelin three-star eatery in New York. Plenty of ladies drop four figures on 40th b-day cruises or beach getaways, I figured, so if I wanted to blow the same kind of cash on an epic meal, bully on me.

©davers/flickr

Unfortunately, it was probably the most disappointing dinner I’ve ever had—not just because the food was woefully subpar, but because spending obscene gobs of money on something only guarantees that you’ll never enjoy that something as much as you feel you ought to.

There were a few worthwhile takeaways, though. I always opt for second-tier restaurants now, which are more affordable and thus more likely to exceed, rather than fall short of, expectations. And I remembered how much it pays to complain courteously. Hence, the aforementioned $600 knocked off the bill.

2. A Pair of [Insert Hot-Shit Shoe Brand Here] Stilettos

Approx. cost: Oh, somewhere north of $300

I’ve honestly blocked out how much my one attempt at sky-high high-fashion pumps cost me several years back. It stings a little less if I glaze over just how much moola I wasted. Needless to say, I wore the shoes once and spent the entire night in agony.

I still wear painful heels; I just spend less on the sadistic privilege of doing so. I’ve also checked around, and it seems every woman has a physically and fiscally painful shoe regret in her past. Why is this splurging no-no the hardest to learn? It’s like our feet are addicted to bad boys, and extravagant heels are Colin Farrell.

3. A Fancy Pen and Pencil Set

Approx. cost: $215

I once foolishly thought that adulthood was about mastering life’s little details—details like owning a set of classy writing utensils for those important documents, storing them carefully, and refilling them properly as needed. So I bought a Cross set (which was lovely, don’t get me wrong) to signify to myself that I was finally a grown-up.

The pen went MIA within a week. Then I remembered that I hate writing in pencil. Now I believe that adulthood is about the big picture, and I steal hotel pens wherever I go.

4. Hot Stone Massage

Approx. cost: $155

I am an unabashed spa junkie. I happily plunk down three figures to have my pore gunk extracted, my limbs ensconced in seaweed, and my backside lashed with palm fronds. I have paid to get my epidermis zapped with shockingly painful currents and I have paid to have my flesh gently kneaded while some guy plays a singing bowl in the corner. But I have never considered my spa splurges a waste of money until I tried a hot stone massage.

The stones stay hot for, what, 27 seconds? Then you’re just a naked idiot lying face down on a table with cold rocks on your spine. Pro tip: Ask your masseuse to run his or her hands under hot water before digging in. Ka-ching! Instant savings!

5. Gel Mani-Pedis

Approx. cost: $65 plus tip

©queenieandthedew/flickr

The only other beauty treatment I regret getting. Gel mani-pedis are three times as expensive as regular mani-pedis and insanely overrated. The polish may not chip, but the one time I tried a gel pedi, an entire slick of color lifted right off one of my toenails less than a week later. Boo.

6. Any Bottle of Wine I’ve Spent More Than $50 on

Approx. cost: More than $50

You, dear reader, are welcome to buy me a bottle of $100 or even $200 wine anytime, and I will enjoy the hell out of if and thank you profusely and think you most kind. But if we’re just talking about a bottle I’m buying for at-home consumption—even if it’s to be enjoyed with friends or my spouse—I’ll stick to $30-ish and under, thanks much. Nobody I know is oenophilic enough to detect any appreciable difference in taste. (In fact, nobody anywhere can tell the difference, many studies have confirmed.) And I don’t want my night ruined by constant thoughts of “Does this really taste $70 better than the $17.99 pinot I had last night?”

7. My Three Unused Wedding Dresses

Approx. cost: $1,600

When I told my husband about this assignment, the first thing he said was, “Are you going to talk about your wedding dresses?” So here goes. Getting to the altar took me five ex-boyfriends and three ex-gowns. The gowns all came at the end, during my one and only engagement to my now husband. Suddenly lacking all faith in my ability to pick out my own clothes, I just kept stockpiling frocks. It all worked out in the end and I love, love, love the dress I wore. In fact, I mainly regret this splurge because my family has never stopped teasing me for it.

8. My Condo

Approx. cost: $149,999

Buying my condo as a single gal in 2007 was me play-acting at being financially knowledgeable. Instead of developing a realistic picture of how a six-figure mortgage would shape my financial future, I just enjoyed spouting astute-sounding turns of phrase like “Real estate may be an investment, but it’s not like you can live in your mutual funds.” (I still don’t know what that means.) I bought right before the market began free-falling; I also bought because I thought it would help me get over a breakup. (My most recent ex lived on the block where I rented, so I had to get the hell out.)

A year later, I was so miserable I moved 1,000 miles away, renting out my condo to a string of sketchy tenants. A disaster all around, but here’s the thing: It really toughened me up as a businesswoman, and I’ve never learned so much about money or myself.

That’s the thing about splurges. They’re lessons disguised as regrets. And that’s priceless.