1. FRIEND, AS A VERB
A common lament in pieces about "kids these days and their social whatsawhozits" is "when did 'friend' become a verb?!" The answer is: Sometime in the 1400s. In the earliest examples of the verb "friend" from the OED, it means to make friends. You could go to a place, and "friend" some people there. It also had the meaning of help someone out, be a friend to them, e.g., "Reports came that the King would friend Lauderdale," an example from 1698.
If you could friend someone, it was only natural, according to the productive rules of English word formation, that you could unfriend them too. The word shows up in this example from 1659: "I Hope, Sir, that we are not mutually Un-friended by this Difference which hath happened betwixt us."
In the 1880s "dude" had a negative, mocking ring to it. A dude was a dandy, someone very particular about clothes, looks, and mannerisms, who affected a sort of exaggerated high-class British persona. As one Brit noted in 1886, "Our novels establish a false ideal in the American imagination, and the result is that mysterious being 'The Dude'." To those out west, it became a word for clueless city-dwellers of all kinds (hence, the dude ranch, for tourists). By the turn of the century it had come to mean any guy, usually a pretty cool one. As one Navy man explained in 1918, "in a gang of snipes there is generally one dude who is known as the 'king snipe'."
Where "dude" goes, "dudery" follows. Here's a phrase from 1889 that sounds completely and utterly current: "The Pharisaical dudery which presumes to deny her [woman] a place in the world... equal with man."
5. HANG OUT
"Hang out" has been used as a verb for passing the time without doing much in particular since at least the 1840s. By the 1860s it was kind of slangy, but not unusual, to ask, "Where do you hang out?"
Puke has been around since the 16th century. While it is often claimed that Shakespeare invented "puke," the word has been found in earlier sources. It meant then what it means now, to vomit. But it also used to be a causative verb, meaning to make someone vomit with a tonic or potion. Your doctor might have you purged, bled, and puked for your own good.
Hipster shows up in a 1941 dictionary of "hash house lingo," meaning "a know-it-all." The words "hip" and "hep" had been around since the early 1900s with the meaning of being up on the latest and knowing what's what. Seems like even at the hash house they got a bit tired of all that hipness.
To me, "babe" in the sense of "hot chick" has a very 1970s ring to it. But this sense of babe has been around since the early 1900s. The OED gives a quote from 1915: "She's some babe."
The application of "funky" to music came during the jazz age and started showing up in print in the 1950s, but the "strong smell" sense had been around long before that. Since the 1600s, "funk" was slang for the stale smell of tobacco smoke, and by extension, anything that stank. Cheeses, rooms, and especially ship's quarters could be described as "funky."
Does "outasight" bring to mind a '60s hippie? Or maybe a '40s big band leader? Instead, imagine a Victorian chap in waistcoast and top hat. The earliest citations for "outasight" come from the 1890s.
No frigging way! Frigging has been around since the late 1500s, though it originally referred to masturbation and would not have made your sentence sound any more polite than it would have with that other word that frigging usually replaces. Since the beginning of the 1900s it has served as the more family-friendly substitute for that other word. In this 1943 quote, it can be seen in action alongside a few other ingenious substitute words: "This shunting frigging new arrangement... has got every flaming thing foxed up."
Booze has been general slang for alcoholic drink at least since the 1850s. It has a longer history as a Middle English verb "bouse," meaning "to drink excessively," that became a part of thieves' and beggars' cant in the 1500s. It was still a word respectable people might not be familiar with up until the 20th century, as illustrated by this quote from 1895: "She heard some men shout that they wanted some more booze. Mr. Justice Wright: 'What?' Mr. Willis: 'Booze, my lord, drink.' Mr. Justice Wright: 'Ah!'"
The application of "fanboy" to comics and science fiction had to wait until the '70s, but before that, there were sports fans, and in 1919 the paper in Decatur, Illinois reported that, "it was a shock to the fan boys when Cincinnati...beat the Chicago White Sox." The first citation for fangirl is from 1934: "Mary... dashed out through the rain so swiftly that only two of the fan-girls caught her."
14. TRICKED OUT
Trick has been used as a verb for dress, adorn, or decorate since the 1500s, and it shows up at various times with up, off, or out. The earliest citation for trick out in the OED comes from 1822: "I must trick out my dwelling with something fantastical."
Legit as a shortening of legitimate has been around since the 1890s. It started as theater slang for things associated with legitimate (as opposed to vaudeville or burlesque) theater. From the 1920s on, it was opposed to underworld or shady occupations or places. If you were "on the legit" you were being honest.
It's been good to be fly since the early 19th century, when it meant sharp or knowledgeable. By the late 1800s, it had taken on connotations of attractiveness and fashionableness as well. These citations from the OED illustrate how fly it was to be fly at the turn of the last century:
"I am speaking now of the young...men about town who think it is awfully 'fly' to know tow-headed actresses, and that to sip crab-apple champagne with the gaudy, vulgar thing in pink tights is just the nobbiest thing on earth." (1879)
"They get in with a lot o' cheap skates and chase around at nights and think they're the real thing... They think they're fly, but they ain't." (1896)
"Jim Blake lived in the country, and though a pretty fly boy among the rustics was not up in the ways of the outside world." (1888)