5 Dating Lessons Learned From The Ever-Quotable Dorothy Parker

Dating is hard. And while we millennials may think it’s especially difficult with the commodification of desire that quick-swiping apps and hookup culture have wrought, the truth is, it’s always been freaking hard. 

Look no further than the words of early 20th-century writer and critic Dorothy Parker to find that angst and doubt in love, sprinkled with a little self-deprecation, is not a new invention. 

It was Parker who coined the phrase, “Men seldom make passes / at girls who wear glasses.” The lines make up the entirety of a poem called “News Item.” The neat, direct lines and title make one imagine that Parker was not admonishing the glasses-wearing women — something this bespectacled writer long thought — but more so the fallibility of humans to place too much importance on looks.

Wry observations abound in the rest of Parker’s poetry and stories. Her self-deprecating humor makes it easy to imagine that she’d skewer Tinder, Bumble, etc., with the same sharp eye, were she alive today. Her legacy remains: Writer Sloane Crosley, who has been hailed as a contemporary Parker, recently named her as an inspiration in a recent episode of the “OTHERPPL” podcast , expressing appreciation for the inimitable Parker line, “You can bring a horticulture but you can’t make her think.” One can spot a tone similar to Parker’s own real, if sometimes bleak, view on love typified by the great @sosadtoday Twitter account  and brands like Stay Home Club that sell shirts emblazoned with a simple message: “Awful.” 

Parker herself might not agree, as she said in an interview with The Paris Review, “Let’s face it, honey, my verse is terribly dated as anything once fashionable is dreadful now.” Still, if reading Dorothy Parker makes you wish she and her wordy sharpness were still around to be your social media soul sister to guide you in this universe, look no further than the legacy she left behind after her death in 1967.

Lesson 1: Don’t get caught up in infatuation. 

Dorothy Parker told it like she saw it, often addressing the brutal truths of love, marriage, relationships, and the hypocritical things humans do and say in the name of finding the one. Take her poem “Unfortunate Coincidence,” from the collection Enough Rope:

By the time you swear you’re his,

     Shivering and sighing,

And he vows his passion is

      Infinite, undying—

Lady, make a note of this:

      One of you is lying.

Tell us how you really feel, Dorothy. She’s Carrie Bradshaw long before “Sex and the City” was a twinkle in HBO’s eye (and with less cloying voice-overs to boot). The takeaway? Sure, it’s easy to get swept up in the throes of new love, but the truth of the matter is that those feelings don’t typically last in the long term. Make sure you’re truly compatible with a partner before professing undying love.

Lesson 2: Put yourself first when dating. 

It can be tempting, when you can see your own singlehood stretching out like an unending, super lonely desert highway before you, to think that you need to change in order to attract someone. Let Parker extinguish that notion in her poem “Indian Summer.”

But now I know the things I know,

     And do the things I do;

And if you do not love me so,

To hell, my love, with you!

The more experience you gain, the better you know yourself; the better you know yourself, the better you’ll be able to determine whether a person is truly worth pursuing.  

Lesson 3: Allow yourself time to grieve after a breakup.

In another poem from Enough Rope, “The False Friends,” Parker muses about advice a brokenhearted narrator receives from friends: “... time could heal a hurt, they said / And time could dim a vow.” If she’d gotten dumped in April, she’d surely be fine in May. 

Nope: “For June was nearly spent away / Before my heart was whole.” If you need to be sad after a relationship is over, be sad. It’s better to discard encouraging “Get out there again!” remarks, or calculations of the proper time to “get over it.” You’ll know when you’re ready to reboot that OkCupid profile.

Lesson 4: Don’t wait for someone to call (or, in 2016, text).

We’ve left so many archaic dating rituals in the past by now, yet the debate over whether or not to call text a love interest lives on. How many days after a first date can you text someone? How many hours should you take to respond to someone so it looks like you’re not just waiting for them to text you? At what point do texts become overeager? Above all: What the hell was that smirking emoji supposed to mean?!

It’s maddening, yet when we we brush away all the tingly-giddy feelings of a new prospect and our reluctance to mess up a delicate connection, we know the truth: If someone likes you, a misplaced eggplant emoji or the overuse of exclamation marks isn’t going to turn them off. 

And if you need more reassurance that it’s way better to simply pick up the phone and get in touch, just read Parker’s story, “A Telephone Call.”

A brief excerpt: 

If I didn’t think about it, maybe the telephone might ring. Sometimes it does that. If I could think of something else. If I could think of something else. Maybe if I counted five hundred by fives, it might ring by that time. I’ll count slowly. I won’t cheat. And if it rings when I get to three hundred, I won’t stop’ I won’t answer until I get to five hundred. Five, ten, fifteen, twenty, twenty-five, thirty ... Oh, please ring. Please.

Lesson 5: Maintain a little healthy cynicism.

Perhaps, when getting a particularly weird message from a suitor, you might have shouted out, “What fresh hell is this?” 

Apparently, Parker answered her door with a similar phrase — “What fresh hell can this be?” — and the other interjection was attributed to the writer in a 1989 biography by Marion Meade titled Dorothy Parker: What Fresh Hell Is This? There’s something about the phrase that maintains a little humor while, at face value, being pessimistic.

So much of dating brings to mind the old “If you don’t laugh, you’ll cry” mantra. Know that you are brave for putting yourself out there, and that bravery brings with it enough mettle to get through the undeniably shitty parts of trying to fall in love.

Don’t despair after an awkward meeting at a bar, a small letdown, a casual ghosting — chalk it up to the “fresh hell” that dating unfortunately and occasionally involves and text your friends for a drink. Dorothy would have your back.