Regret #1: The Money You'll Never Get Back

We've all had moments of money-spending psychosis, when we do things like pay $100 to join a weird philosophy club because he belongs to it. Even though we know nothing about philosophy other than that it can probably be gotten for free. Good thing we can use our new philosophical skills to construct the following aphorism: "It is not about how much money I have paid; it is about the price I am paying never to think about him again."

Regret #2: The Thing You Can't Erase

You've spent countless hours polishing your LinkedIn profile, and yet the first thing that comes up when someone Googles your name is the virulent comment you left—with your entire moniker as user name—on a news article that rubbed you the wrong way on the wrong day, the comment that sparked a frenzied debate for inches and inches and inches. There's no deleting it. But there are other ways, such as removing yourself from search engines or hiring a professional company to do the long, complex, frustrating work for you.

Regret #3: The 3rd-Date Sleepover

It seemed like a good idea at the time, like so many ideas do at post-martini-o'clock, and then you woke up in a strange apartment, feeling like one of Don Draper's tousled consorts. But listen, studies have shown that while women tend to regret their casual sexual encounters, men only regret the times they didn't sleep around. In other words, he doesn't think any less of you. Your remorse is largely evolutionary.

Regret #4: The February Short Shorts

We've all woken up in the middle of the night, full of terror, wondering: "Did I actually wear short shorts over tights? In the middle of the winter? To WORK?" But whatever the fashion misstep—from platform combat boots to overly ambitious shoulder pads—the beautiful thing about fashion is that it's temporary.

Regret #5: Choosing Love Over Money

Ah, the fever of first love, when you can hardly see straight through your cataracts of joy, and so you think, "What career in Chicago? Of course I want to join this amazing man in rural Alabama!" Twenty years later, you're wondering about what life could have been had you stayed at your old, kind-of-glamorous law firm. But keep in mind: Research shows that what Americans regretted most—and most intensely—were the times they prioritized their jobs over their relationships. Statistically speaking, you made the right choice.

Regret #6: The Thing You Can Still Apologize For

The engagement you called off, the honest mistake, the cruel thing you said: Chances are, even if you have to muster up every scrap of strength, swallow every sip of pride, you can still apologize. Even if you have to fly across the country. Even if you have to show up at somebody's door. Even if you have to say I'm sorry until your lips go blue. It's a failproof phrase. You aren't always forgiven—but it does help you to forgive yourself.

Amy Shearn is the author of The Mermaid of Brooklyn and How Far Is the Ocean from Here.


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