Dateland: The Best Breakups

Some friends and I were reminiscing about our favorite breakups. The most spectacular ones in terms of raw drama took place in our 20s, and the saddest, most soul crushing ones happened in our mid 40s. When you’re in your 20s, breakups are kind of fun. They typically happen in public places with tons of interested spectators. Everyone takes sides and someone usually gets a beer tossed on them. The older you get, the less fun it is. You are now an adult and realize that feelings aren’t recyclable plastic bottles to be tossed away in the hopes that they will be transformed into something really cool at a later date.

I was chatting with a friend who just turned 50 and is recovering from the end of a 12-year-relationship.  This friend, who we’ll call Twinkie, was a breakup legend in her 20’s and 30’s. We would encourage her to date the most wildly inappropriate girls simply to have the joy and drama of experiencing the inevitable bust up.

When not in love, Twinkie is reasonable and quite sane. But when crushed out, she’s quite the kook. She loves the big first date. No movie and dinner for the Twink! Bring on the private jet that whisks her and her beloved to an exclusive concert or an over-the-top dinner at her palatial home served by her butler. Yes, she has a butler. She always referred to him as her handyman until I suggested she start calling him her butler, because he is always lurking around the house, eavesdropping on our conversations and serving us snacks.  Plus, I’m fairly certain he’s capable of murder, and I’ve always longed to say “the butler did it.”

Her full-on press tends to frighten new prey and they have a tendency to stop answering her calls after the first blizzard of roses from the florist. The cold shoulder is catnip to the Twink! Unrequited love tips her into full obsession, and she’d embark on madcapped missions to stalk, charm, cajole, threaten, and entrap her love object. And, weirdly, her method nearly always worked. The girl would be so exhausted trying to avoid the Twink that she’d finally acquiesce for no other reason than to get some sleep.

All would be swell until the breakup. At the first hint of instability in the relationship, Twink’s focus would intensify to the type of single-minded fixation that she shares with certain third-world despots. My favorite Twink breakup story involves her buying out the world’s supply of the type of vibrator her ex favored and piling them in her garage, just like Saddam Hussein did with the weapons of mass destruction. She then commanded her butler to break into her ex’s house and steal the last remaining vibrator from the ex’s bed stand. It all ended up in court, where the Twink’s lawyer merrily waved the vibrator in front of the jury. I never understood that move, since the vibrator evidence was clearly not in the Twink’s favor. But it made the jury laugh, and the case was tossed on the grounds that it was completely ludicrous.

When I heard that the Twink’s latest relationship had ended, I called her to commiserate. She spoke half-heartedly of the revenge she was seeking—most of which had to do with raiding retirement funds and deliberately torpedoing real estate investments. I was horrified by her anemic efforts.

“Twink, what’s become of you? No police? No restraining order? No bloodshed?” I asked.

“Eh, I’m old now, and I’ve got high cholesterol,” she explained with a shrug. “I’ll let the lawyers fight it out.” But then, as I mourned for our lost youth and misguided passion, I heard a shrill yip from the closet.

“Twink! You stole her dog!” I exclaimed.

“I might have high cholesterol, but I’m not dead yet,” she said with a cackle.

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