Dating’s Best And Worst Moments—Ever

Dating’s Best And Worst Moments—Ever

We went spanning the globe—and the centuries—to bring you this highly opinionated timeline of romance’s highs and lows.

By Daniel Radosh
The Best The Worst
4 Cleopatra seduces Mark Anthony, circa 42 B.C.
The Queen of Egypt and the leader of Rome had originally convened to discuss state affairs, but ended up engaging in more pillow-talk than politics, showing that love truly can change the course of history.
4 The Duke of Orleans pens the first Valentine, 1415.
While imprisoned in the Tower of London, Duke Charles writes the first known Valentine’s Day poem for his wife. His amorous letters set the example for centuries of lovers, including those not behind bars.
4 Invention of America’s first breath freshener, 1890s.
This honor goes to a licorice-and-herb concoction called Sen-Sen. Kissing would get even sweeter after Certs arrived in 1956, then Tic Tacs in 1969, and the minty breath spray Binaca in the 70s.
4 Debut of the first movie date, 1921.
Before then, flicks were male-oriented Westerns and comedies; but The Sheik had elements of adventure for the gents and romance (and actor Rudolph Valentino) for the ladies. Was it a success? Well, it is the only movie with a condom named after it.
4 Creation of Sadie Hawkins Day, 1937.Women were encouraged to (gasp) ask men out on dates. First celebrated in a Li’l Abner comic strip, Sadie Hawkins Day soon spread to high schools and colleges across America. Sure, it was only one day, but you gotta start somewhere.
4 Introduction of the Pill, 1960.
And with it came the advent of a sexual revolution, in which women could jump into bed whenever they were ready, with no break in the action for contraception.
4 The first computer dating service, 1965.
Launched by Harvard and M.I.T., this service became an enormous success as soon as people realized that the computers didn’t just match you up with Harvard and M.I.T. students. From there, it was a straight shot to the wonderful world of online dating.
4 The Stonewall Riots, 1969.
Raids on gay bars had been a fact of life for the homosexual community. But, after 2,000 people in New York City’s Greenwich Village fought back when police tried to shut down the Stonewall, the gay community banded together nationwide, and dating became at least a little bit easier.
4 Starbucks is born, 1971.
And the quick, cheap, informal coffee date transforms into the cozy, expensive, all-afternoon cappuccino date. Great for a while, but there are now over 12,000 Starbucks worldwide, meaning an invitation to one is the first warning sign your date has no imagination.
4 Barry White’s album I’ve Got So Much to Give is released, 1973.
The disk could make the difference between a date ending in 10 minutes or the next morning.
1 Creation of the first mass-produced Valentine’s Day card, 1850.
Thank Esther Howland for that. Why send a personal expression of your devotion when you can send a cliché?
2 The beginning of 14 years of Prohibition, 1919.
Dating is hard enough, but without a little booze—to help things along at the beginning, to celebrate in the middle, to dull the pain afterwards—it’s damn near impossible.
3 Debut of The Dating Game, 1965.
At the time, it was considered the most degrading form of televised entertainment imaginable (“Bachelor Number One, I play the trombone. If I blew you, what would you sound like?”) Now, we know its real crime was setting the bar so low for the countless bottom-feeding reality-dating shows to come. Average Joe, Third Wheel, Who Wants to Marry a Millionaire? It all started here.
4 The dawning of the cell-phone era, 1973.
Motorola employee Martin Cooper places the first cell-phone call ever to rival AT&T’s Bell Labs while walking the streets of New York. What’s that got to do with the downfall of dating? Soon, not showing up on time for a date becomes excusable, just as long as you call.
5 Looking for Mr. Goodbar, 1975.
The best-selling novel and hit film based on a true story, portray the dark side of dating: Singles bars and one-night stands sure aren’t fun if you get stabbed to death.
6 Ladies’ Night is declared illegal in Long Island, New York, 1981.
A tavern offering Ladies’ Nights is cited for discrimination against men, unless it offers the same number of Gentlemen’s Nights. In the coming years, several other states followed suit with similar cases. (Let’s just say it’s one of those laws many bar owners ignore.)
7 Karaoke makes its U.S. debut, 1984.
Sure, it’s great for a night out with friends, but the rise of the karaoke date has been a disaster. Making a fool of yourself and mocking other people does not equal romance.
8 My date with Heather Jensen, senior year, 1987.
Don’t ask.
9 Speed-dating starts to sweep America, 1998.
A California rabbi invented the concept of rotating 3-to-10-minute dates, but honestly, who wants to get to know someone over a stopwatch?
10 Conspicuous liquid consumption, 2002.
Sold for $50 a glass, a drink considered the world’s most expensive cocktail becomes available at—where else?—New York’s Trump World Tower. Nothing makes for a bad date like trying too hard to impress.
Daniel Radosh is contributing editor at The Week and a freelance writer. He lovingly tends a blog at
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