Sherman Ave's Totally Not Creepy Guide to Chatting Up the Ladies

Sherman Ave's Totally Not Creepy Guide to Chatting Up the Ladies

  (via goodnewsweekly.ca)

Summer’s here and so is she, boys: Your sundress-sporting, wavy-haired Aphrodite, and she’s gliding towards you in all her glory. You could totally get it right here and now, if she wasn’t a complete stranger. But she is, and you’ve got only seconds to impress her, so there’s no time for classical seduction methods like skywriting or murdering her other suitors - you’ve got to act now. Sure, maybe actions speak louder than words, but what if the words you’re saying are really loud? Quick, yell some shit at her, maybe she’ll sleep with you!


Option 1: The Question

Pros: Not only are you preparing her for entrance into a job market predominantly dominated by men who she’ll have to answer questions for in order to gain employment, you’ll also find out more about your potential lady-love. What is her name? Where is she going? Why won’t she smile for you so you can see those pretty teeth?

Cons: Remember pre-Brad Angelina Jolie? She made out with her brother and wore a necklace filled with Billy Bob Thornton’s blood. Hot does not necessarily mean sane. Maybe you don’t want to know where’s she’s going because it involves drowning kittens or looking for the number 23 or setting small fires. Maybe you don’t want her to smile because her teeth have been filed to shark-like points. Maybe you don’t want to know her name because it’s something weird like Gertrude and she doesn’t even go by her middle name or anything and that’s a total deal-breaker.

Option 2: The “Hey!” or Similar Exclamation

Pros: This one’s all about plausible deniability. If she responds positively, go for the jugular and chat the babe up! If she looks over with an expression of disgust or fear, just play it cool and act like you’re really excited about something you just read on your phone. “Wow! Be yourself, everyone else is already taken? Oscar Wilde was so smart.”

Cons: Random greetings can sometimes attract unwarranted attention, especially from people who you could conceivably be yelling to, leading to an entirely unwanted interaction with Craig from your Psych class because yeah, ha ha, you thought the midterm was “hard as shit” but that’s not really what you’re trying to talk about right now, okay man?

Option 3: The Smiling, Intense Eye Contact While Muttering Suggestively Among Friends

Pros: This approach shares many of the advantages of the vaguely directed “Hey!” because it offers the same level of ambiguity. The muttering makes your conversation unidentifiable enough to give you and your crew a mysterious aura. Maybe you’re talking about how hot she is, but maybe you’re just telling a racist joke that you don’t want everyone around you to hear. Chicks dig the whole “mystery” thing.


The real Pussy Wagon.


Cons: DO NOT TRY THIS ALONE. Your older brother was right, talking to yourself makes you look like a fucking freak. You want to hit on this girl, not lock her in your basement and make her watch every episode of X-Files with you, even the ones where Mulder gets abducted by aliens and Scully has to team up with the T-1000. Also, unlike the other options presented, this one lacks the volume advantage. Try pointing directly at her to clear up any confusion if she doesn’t seem receptive.

Option 4: The Compliment

Pros: Everyone knows the female ego is founded entirely on male compliments and that the all-time best male compliment is to tell a female that she resembles a celebrity well known for her sex symbol status, like Scarlett Johansson or Justice Ruth Bader Ginsberg. Why not give the girl what she wants?

Cons: Not all compliments were created equal. Think before you speak, because it’s easy for your words to be misinterpreted as much creepier than they actually are. You’d be amazed how easy it is for a girl to imagine you picking her used tissues out of the trashcan and saving them when all you even said was that she has “very supple breasts.”


When things are all said and done, yelling at girls when they’re trying to run some errands or go for a leisurely stroll or do absolutely anything that doesn’t involve getting hit on is not the best way to catch that special someone’s eye. Instead, follow her home and write down her address and Google it using one of those property ownership information websites and find her on Facebook and find out where she works and call the place and ask when she’s working because you’re “her cousin and you haven’t seen her in a long time and really want to surprise her” and show up at the end of her shift and walk into her by mistake so that she spills a drink or drops a stack of papers and apologize for your endearing clumsiness and offer to make up for it with a couple of drinks or maybe even dinner because you know this great Italian place a few blocks away that has amazing mozzarella sticks like a normal person.

Missed Connection: White girl in the Deuce Bathroom – w4w – 20 (Evanston)

Missed Connection: White girl in the Deuce Bathroom – w4w – 20 (Evanston)

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