Noun: Ancient file-sending sorcery now called Hightail. Back in the early 2000s, before Google Drive or Dropbox, Yousendit was the go-to website for sending big files that your AOL inbox couldn’t handle. Saying “I’ll Yousendit to you” basically meant “I’ll email it, but cooler.”
Verb: To share large files online in an unnecessarily nostalgic way.
Internet ancestor alert. Fun fact (or urban myth): the name YouSendIt helped inspire a certain naming trend on the early web — think YouTube, YouPorn, YouNameIt. It was the “You” era of the internet, where every site acted like it was personally talking to you.
Verb: To share large files online in an unnecessarily nostalgic way.
Internet ancestor alert. Fun fact (or urban myth): the name YouSendIt helped inspire a certain naming trend on the early web — think YouTube, YouPorn, YouNameIt. It was the “You” era of the internet, where every site acted like it was personally talking to you.
Friend 1: “The file’s too big for email.”
Friend 2: “No worries, I’ll Yousendit to you like it’s 2005.”
“Before Dropbox existed, my band’s demo only survived thanks to Yousendit. RIP to a real one.”
Coworker: “Can you share the presentation?”
You: “Sure thing, let me Yousendit that bad boy.”
“Grandpa doesn’t trust the cloud, he still asks me to Yousendit stuff.”
“Back then, if someone Yousentit to you, you knew they were serious about getting that file to you.”
Friend 2: “No worries, I’ll Yousendit to you like it’s 2005.”
“Before Dropbox existed, my band’s demo only survived thanks to Yousendit. RIP to a real one.”
Coworker: “Can you share the presentation?”
You: “Sure thing, let me Yousendit that bad boy.”
“Grandpa doesn’t trust the cloud, he still asks me to Yousendit stuff.”
“Back then, if someone Yousentit to you, you knew they were serious about getting that file to you.”
by EMD F59PHI October 24, 2025
Get the Yousenditmug.