How Women Used To Trick Men Into Asking Them Out

By Molly Farinholt··  3 min read
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How Women Used To Trick Men Into Asking Them Out

Back in the day, there was no “sliding into DMs” or sending texts with flirtatious emojis. Women were a bit more creative with their modes of capturing the attention of men. These tricks might be considered out of style now, but why not bring them back?

Here are five ways women used to “trick” men into asking them out. 

Dropping the Handkerchief

This trick dates back to Jane Austen’s time. Women would drop their handkerchief so the man who had caught their attention would see it, retrieve it, and chase after them to return it. Conversation and much flirtation would (hopefully) ensue. 

mr wickham picks up hankerchief

Most women don’t carry handkerchiefs anymore, but that’s not to say that you can’t try this out. Instead of dropping a handkerchief, drop another small object such as a pen (think Cher from Clueless), library card, or that mysterious key on your keyring (does it open the mailbox at your old apartment or the back door at your parents’ summer house?). Hopefully, that cute guy who lives two doors down will pick it up and, after returning it to you, strike up a conversation that leads to an invitation to dinner!

cher drops pink pen

Passing a Note

Passing notes is a lost art. Folded-up sheets of paper scrawled with sweet and endearing messages were once a sure way to win a man’s attention. Nowadays, we labor over whether or not to send him a text message. Way back when, women kept it thoughtful and direct with the handwritten, hand-delivered (even if it was delivered by a friend) letter. It doesn’t have to be long or poetic, but a note shows a sort of confidence that a man will have a hard time ignoring. 

writing a love letter

Just Happening To Be Where He Is

Think Lydia and Catherine Bennet from Pride and Prejudice — but maybe a little less flighty and eager. The two younger Bennet sisters made sure to be where the handsome militia officers were, flaunting their finest dresses and singleness.

lydia a whole campful of soldiers

It’s not a bad move if done properly — with tact and graceful reserve. If the one you’re after is planning to be at the work Christmas party, you should absolutely attend, wearing a classy black dress. 

Acting the Damsel in Distress

Men love to be knights in shining armor, and women once capitalized on this by acting the part of the damsel in distress. In The Princess Bride, Westley saves Buttercup countless times, proving himself worthy of her love.

wesley sand pit save

An act of heroism makes a man feel extra manly and surely opens his eyes to the beautiful woman he’s rescuing. You don’t have to do anything drastic, but even something as small as pretending that you’re lost and in need of directions can be a perfect avenue to capturing the handsome stranger’s attention.

Taking Up His Hobby 

Everyone loves the classic (and extremely cheesy) “let me show you how to properly swing a baseball bat” move. Showing interest in the cute guy’s hobby — and needing (or “needing”) lessons on how it’s done — will never stop working. It allows a man to display his expertise and you to look interested. And, of course, it sets the stage for some flirtatious physical contact. 

princess diary archery lesson

Honorable Mentions

If all else fails, these two classic moves may work. 

The “Grease” Makeover

Sandy really got Danny’s attention with her transformation from a poodle-skirt-wearing goody two shoes to a cigarette-smoking, high-heel-wearing woman. We’re not suggesting that you go this far, but the new hairdo and high heels might work some magic. 

sandy makeover grease

The “Bend and Snap”

Finally, Elle Woods’ “bend and snap” move is rumored to be foolproof. Rewatch the scene from “Legally Blonde” to get the technique down. 

Closing Thoughts

Instead of stalking his Instagram and giving his photos the occasional like, why not try these bolder moves to get his attention? 

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Seek Truth. Find Beauty.

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