Match has two definitions: the "thing you light on fire" and a "competition". Despite being homonyms, their etymologies can be followed back to completely different language families. The former definition, "a fire stick", comes from the Old English word macche, or "wick", which metynomically shifted to its current meaning. This is from Latin myxa ("wick"), from Greek muxa (you guessed it... "wick"), which finally changed definitions completely as we move backwards to around the sixth century BC, as mukes, "snot", was in use. The term came to be applied to the wax because of the similar composition, and comes from PIE mewk, meaning "slime". Now to the "competition" part of match. Back in the day, its only definition was "an equal" (that meaning remains today), and in a surprisingly tolerant display this extended to the connotation of "husband" or "wife". Keep in mind that this is in the Middle Ages. Wow. Anyway, phonetically this changed to maecca, "mate", from gamakon, or "fitting well together". This is from the Proto-Indo-European word mag, or "to fit". It's fascinating how match and match fail to match in their origins.

The person who asked for this word etymologized is a genius of ironical humor. Today meaning "asking for something", request came from the French word requeste, defined as the noun form of "request", showing how the word verbified over time. This is from Latin requista, "a thing asked for", which derives from the earlier word requirere, cognate and etymon of the current word require (through French requerre). Here we eliminate the obvious prefix: re- was attached to the root quarere, which meant "question" but originally also meant "to ask". This is interesting because the semantics shifted from "ask" to "give", seemingly an about-face but really an innocuous transition. The origin here is labeled "uncertain" but is in fact generally agreed upon by etymologists: through Proto-Italic kwaiseo, we can trace the stem of request to the Proto-Indo-European inquisitive pronoun kwo. Fascinating.

My mother, for whom English is a second language, frequently misappropriates the terms obstacle and obstruct to create the imaginary word obstrucle. This provoked an interesting thought: both words cover similar concepts and sound similar, so are they etymologically related? Turns out the two are more like cousins than brothers. Obstruct is from the Latin word obstruere, which meant "hinder" and is a portmanteau of the prefix ob- ("against") and struere, or "to build". Thus an obstacle hindered building. Struere is from the Latin word for "heap", strues, from the Proto-Italic term strowo, meaning "pile up", which in turn derives from the Proto-Indo-European root strew, which meant "to spread". Semantic connections are clear. Next is the word obstacle. This is through French and traces to the Latin noun obstaculum, which meant "a hindrance", a combination of ob- (the same root as before), -culum (a suffix), and sto, or "to stand". Sto, being the root I'm etymologizing, is from the Proto-Indo-European root sta, also "to stand". Thus it may be concluded that despite their close definitions describing hindrances, all obstacle and obstruct have in common are the first two  letters, which define the words, since as a morpheme they mean "against". Nothing else in common: wow!

The word ennui is surprisingly little-known. Meaning "a feeling of dissatisfaction or boredom", it comes from the Old French word enui, meaning "annoyance", since something that is annoying quickly becomes boring and dissatisfying. This is from the earlier root enoiier, meaning "bother", which in turn derives from Latin inodiare, or "to make loathsome". This is a combination of the modifier in- and the stem odiare, or "hate" (the connection is easy enough to see). This is from the earlier word meaning "hate", odio, from the root odi, which, as many Latin words do, traces to Proto-Italic, in this case the term odai, which is ultimately from the reconstructed Proto-Indo-European word which sounded something like od and also meant "hate". You can see that this word changed rather drastically towards gentrification; going from a strong, ancient feeling to a more modern, complex, and softer concept, showing how humanity changed along with the word.

The word pauper ("poor person") is the source of several English words and phrases. Itself from Latin paupus, a little-used word which meant "alcoholic uncle", which in turn came from the Proto-Indo-European root pap ("male relative"; also the root of today's word papa, and Latin pater, "father"), pauper was first coined by King Richard III to describe his lesser-known uncle on his mother's side, Prince Brad II, who was forced out of line to the royal throne and into life as a serf; thus the connection was made. 300 years later, William Shakespeare was the first to use the word pop: influenced by pauper, it remains as the word we know today ("to make a light sound"), because one of Shakespeare's favorite pastimes was the sport he named popping, where the objective was to poke a poor person with a sword until they died. Pop became the genre of music from this definition, since it described "sounds" and songs have sounds. Another derivative of pauper is hippopotamus. While this may seem rather shocking, it actually makes quite a bit of sense. Hippopotami have large hips, and so the word was added to "poor person" (since hippopotami have no possessions, they were named "poor" when they were first discovered by Charles Darwin) to make the word we know today. The last word which we all know came from pauper is gullible. As we all know, British people have weird accents, and London local dialects switch p's with g's and double l's, creating the now widely used word gauller to describe a poor person. Next came two changes: the initial a was dropped due to a typographical error in 1945, and the word began to semantically shift towards the meaning of "credulous", since the rich people who used the word pauper looked down upon poorer people as easily duped. Since the term now applied to a concept and not a person, folk etymology gradually switched the -er suffix of guller and added an -ible suffix, because that just sounded right. It's pretty crazy; the connections between pauper, pop, hippopotamus, and gullible sound almost made up!