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Heyy, or other iterations of the word "hey" with two or more y's at the end, is an Internet slang term that can be interpreted as a flirtatious greeting, especially when said in private via texting or instant messaging. While its usage is heavily context-dependent and its meaning still contested, the notion has gained traction on the social media since as early as 2010.
While appending vowel letters (ex: hii, heyy, oooh) in online communications has been observed as a casual practice since the early years of instant messaging in the late 1990s, the ambiguity of its meaning didn't arise until the advent of QWERTY smartphones and autocorrection almost a decade later, which made unconventional typing of common words like "heyy" a far more deliberate of a practice. The earliest known mention of its flirtatious connotation was can be found in an Urban Dictionary entry for "heyy" submitted on March 22, 2009, describing it as:
A more sexual version of hey. Don't get confused with heey which is a more friendly version of hey and has no sexual reference. watch out though, it could just be a spelling error.
In June 2010, Yahoo Answers user Alex M posted a thread asking how to interpret a text with two y's from someone of romantic interest, to which user MissMablee explained:
"Heyy" is more flirty than just "Hey." Just "Hey" can sometimes be a sign of disinterest so when a girl says "Heyyy" it could sometimes show that she is more interested than a girl saying "Hey" And most of the time, this all doesn't matter. Every girl's texting style is different. So you can't really tell if they're interested just by reading between the lines of text messaging.
In 2011, dozens of similar Q&A and discussion threads about the potential double meaning of "heyy" with two y's surfaced on Yahoo Answers, Quora Bodybuilding.com Forum and Reddit, as well as numerous other male dating advice forums. On July 10th, 2011, Redditor /u/IsThatEvenLegal submitted an /r/AskReddit thread titled "Whats the difference between 'Hey' and 'Heyy,'" to which /u/kruce responded:
"Heyy means you're happier to talk to the person than hey. It implies a voice inflection.
In August 2011, Tumblr blog MaleMinded posted an infographic illustrating a range of subtleties implied by the addition of extra y's at the end of "hey." The post, which has been since removed, soon went viral on the platform and subsequently picked up by Gizmodo and BuzzFeed.
In 2012, a number of jokes about the texting practice sprang up on the social media, with many using "the D" and "come over bae" as the punchlines.
In September 2017, the axiom was used as a plot twist in Season 1, Episode 2 of the true crime mockumentary TV series American Vandal, wherein the investigation takes a new turn after the filmmakers discover that Sara, a popular student in their high school, had texted Alex Trimboli, an outcast outside of her circle, a "heyy" with two y's in the past.
 Quora – What does it mean when a girl texts “heyy”?
 Gizmodo storybreak stars
 Yahoo – what do people mean when they put an extra y to hey? | Yahoo Answers
 Yahoo – why do girls put 2 y's at the end of a hey? | Yahoo Answers
 Bodybuilding.com – if a girl says hey with 2 extra y's – Bodybuilding.com Forums
 Yahoo – When a girl says this through text, what does it mean?
 Yahoo – Search Results for 'Heyy With Two ys
 Reddit – Search Results for 'Heyy With Two ys
 Tumblr – Maleminded / Texting
 BuzzFeed – What Texting 'Heyyyyy' Means
 Odyssey – 10 Texts Every College Girl Has Gotten From The Typical Guy
 TV Time – A Limp Alibi
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