By the way the exact meanings and origins of most of these words, or sayings, are greatly debated over, so you may disagree with some of what I write, but I'm simply reporting on what I have researched.
Achilles Heel
This saying comes from Greek mythology. Achilles was held onto by his mother, Thetis, by the heel as she submerged him into a river. While in the river Achilles could survive, the only part of him that was exposed was his heel. Eventually Achilles died because someone shot him in the heel, the only place he was vulnerable. "Achilles Heel" is the same as saying you still have a vulnerable part of you.
Bakers Dozen
People always take this meaning to be a number that is 13. This is true, but there is also a story behind it. Sometime ago in history bakers often sold 12 loaves of bread to nobles but he could be severely punished if his loaves were underweight. So, to be above suspicion, a baker would make 13 loaves rather than just 12.
Beat About the Bush
You've heard the saying, "I'm not going to beat round the bush." Hunters used to beat around bushes to make birds hiding in them fly out. So to "not beat around the bush" means they are going to get right to the point and to "beat around the bush" means not getting to the point.
Bee Line
In the past people used to believe that bees flew in a straight line to get to their hives. Therefore to make a "bee line" to go somewhere means to go straight there, without side trips or stops.
Break a Leg
There are many explanations to this saying but I will tell you about the one I happen to like the best. After a Shakespearean play the audience would either throw coins and flowers if they liked it or rotten food if they did not. If they did like it and threw coins the actors would have to bend over to pick up the coins then it would appear they were breaking a leg to do so, meaning you would want to "break a leg" during or after a performance.
A Biter Being Bitten
This saying is another old one. A "biter" was a con man. Therefore "a biter being bitten" was the same as a con man being beaten at his own game.
to Boot
Oddly enough this has nothing to do with the boots you put on your feet. The word was originally "bot" which meant profit or advantage. So to get something "to boot" means you get extra.
Chap
I know this is not a saying but a single word (I'm going to have a few of these). "Chap" is shortened from the word "chapman" originally "ceapman" which meant merchant or trader.
Chew the Fat
When guests would come a-visiting their host would give them a piece of bacon. During their visit the guest would chew on the fat.
Copper or Cop
Cop is the word for a police officer and the word "cop" meant "to grab" therefore a copper was someone who "grabbed" the criminals. So it's not necessarily a derogatory term like the saying "fuzz" is. (Fuzz has several different meanings but one of them is "fussy" meaning that policeman are hard to please. Another supposed meaning is that it's a slurred pronunciation of "feds". But who really knows?)
Cut and Run
During an emergency sailors would want to leave quickly. So instead of winding up the anchor that was dropped they would simply cut the rope and flee.
What the Dickens?
Many people suppose that this phrase was started because of the writer Charles Dickens, but indeed it is much older than that. In fact as far as we know the saying was started in the 16th century and "dickens" means "devil". So it's the same as saying, "What the devil?"
Don't Look a Gift Horse in the Mouth
I have never heard this one till today, and it has a rather interesting meaning. If someone gave you a horse and told you the age, they could have been lying. By looking at a horse's teeth you can determine it's real age. Therefore if you get a gift don't examine it too closely. It's my goal to say this to someone by the end of the week. There is another saying that was derived from this saying and means the same thing. From the Horses Mouth
Eat, Drink and be Merry
This saying comes from the Bible. In Ecclesiastes it says "the man has no better thing under the sun than to eat, drink and be merry".
Fiddle While Rome Burns
There is a legend that in 64 AD Emperor Nero played the lyre (the saying turned into fiddle because who plays a lyre anymore?) while Rome was burning. However if this is actually true or not, no one can say. This is the same as doing something cruel and walking away from the situation while not caring.
Flying Colours
After a great success a fleet of ships would return to their harbors with their colours proudly flying on their masts. So if you have had a great victory, and are proud about it, you have done it with "flying colours".
Frog in Your Throat
Have a frog in your throat? I sure hope not. During the Medieval era physicians believed that if you had a cough or sore throat that putting a frog in your mouth would help relieve the pain and coat the throat. They would put the frog in your mouth and remove it when they believed it had helped all it could.
Get Out on the Wrong Side of Bed
It's been superstition for some time that setting down your left foot first when you get out of bed is bad luck, and will continue to be so till you go to bed again, the next night.
Get the Sack or to Get Sacked
In the past workers kept their tools in a sack. If their employer or boss gave them their sack that meant it was time to pack up and go, you were... Finished. Fired. Sacked. History.
Give Somebody a Cold Shoulder
This is such an odd saying and has such a fastening origin. A long time ago if you had an unwanted visitor and they stayed for a meal you would give them a cold shoulder of mutton, not some hot meat from a better part of the body. This was a little hint that you didn't like them and didn't want them back.
Go the Extra Mile
This means that you need to force yourself to go another mile, even if you want to give up. It originated in ancient Rome when Romans, by law, could make anyone carry things from them for one mile. In Matthew 5:41 Jesus told his followers 'if somebody forces you to go 1 mile go 2 miles with him'.
Goodbye
Yeah this seems like a dumb one to put up. "Goodbye" is a way of saying "farewell". It's the same as saying "I'm glad I was here, it was good, bye!" But it really is a shortening of the saying, "God be with ye." Someone, sometime must have slurred the four words together, is all I can guess.
Hobsons Choice
In the 1600s when you wanted to go on a long journey you could rent a horse. The reasoning behind this was you could rent a horse that was not your own and you didn't have to let your own horse get worn out or hurt during travel over rough roads. There was a man during this time by the name of Thomas Hobson. He rented out horses to people and many times did not let them choose which horse they could rent, so they had no choice in the matter. This phrase has been used ever since if you have no choice in a matter. You have "Hobsons choice." Another saying I want to use on someone before the end of the week.
Holier than Thou
This is another Biblical saying. Isaiah 65:5 it says to not be like people who say, "come not near me for I am holier than thou". Because that is simply not true.
Honeymoon
"Moon" has been the word for "month" in many cultures throughout history. So "honeymoon" simply means "month of honey". In history it was traditional for newly weds to spend their first month of marriage drinking honey mead. I'm unsure as to the reason of this tradition.
By Hook or by Crook
This saying most likely comes from a law that was established in Medieval times. It stated that a shepherd could use fire wood of any branches they could be reached on tree with their crooks or their billhooks.
Humble Pie
The word "humble" in this saying was originally "umble". The umbles were intestines or the less-than-delicious parts of an animal and were eaten in pies by poorer people and rich people's servants. After a deer was slaughtered all the delicious, tender parts went to the rich, all the leftover went to their servants and poor people. So to eat this umble pie you had to humble your self and show that you were not too high-and-mighty.
Kick the Bucket
When slaughtering a pig you tied it to a wooden beam, which in French is "buquet". As it died it kicked the buquet and the saying slowly became "kicked the bucket". So in reality it has nothing to do with buckets.
Know the Ropes
Often times this saying is used when someone is trying to teach someone a job. During the times of wooden ships and masts their were many, many ropes that were needed and the sailors would have to know the purpose of each rope and where it went and how to use it correctly to keep everything working. So they had to "know the ropes".
Let the Cat Out of the Bag
At one point in time when selling piglets people would place the piglets in a bag. Sometimes, instead of selling piglets people would sell kittens, which make similar sounds to piglets but if you let the cat out of the bag the trick was exposed. Therefore when someone "let's the cat out of the bag" they are blabbing a secret or exposing a falsehood.
Lick into Shape
This saying, I find, to be rather comical. In the Middle Ages people believed that when a bear cub was born it was shapeless, like a blob, and the mother would lick them till they were the right shape.
A Little Bird Told Me
This saying comes from the Bible. In Ecclesiastes 10:20 the writer says not to curse kings or the rich in private because "a bird of the air" may report what you say.
It's a Long Shot
In the past guns were not nearly as accurate as they are today. So if someone was standing at a long distance and fired, it was not very likely that they would hit their target. If someone tells you "it's a long sh0t" it means there's not much of a chance or there's little hope of it every happening.
Moot Point
The word "moot" is a Saxon word for "meeting" or "discussion". So a point that needs to be discussed is "moot".
Nickname
"Nickname" is a derivative of the word "ekename" which means "alternative name".
No Rest for the Wicked
This is yet another saying that comes from the Bible. In Isaiah it's written, "'The wicked are like the tossing sea; for it cannot be quiet,and its waters toss up mire and dirt. There is no peace,' says my God, 'for the wicked.'" (English Standard Version)
Pearls Before Swine
It's truly amazing how many sayings originated from the Bible. This saying came from a quote in Matthew 7:6. Jesus says, "not to give dogs what is holy and to not throw pearls (which means 'wisdom') before swine (which was very insulting and meant 'the ungodly')." (English Standard Version) So it's the same as saying "don't throw away Godly wisdom on those who don't know God and don't want to know God."
Peeping Tom
The story behind this saying is a little odd and a little funny. According to legend a man by the name of Leofric taxed the people of Coventry, too much. Angered his wife, Lady Godiva, told him to stop taxing his people so heavily. Leofric told his wife that he would, indeed, lower the taxes if she were to ride through the town on a horse, and be completely naked. The name "Tom" was added later to the story. As the story goes everyone in the town was supposed to stay inside and close all their shutters and not to look outside. (Which seems to me defeats the whole purpose of Leofric's request, but what do I know?) But one man by the name of "Thomas" peaked while Lady Godiva was riding by, and this earned the fictional character the name of "peeping Tom".
Pot Luck
When people would meet together they would bring food to share and it would all go into one large pot. You would have to be lucky to have a good bowl of whatever was in the pot, since who knows what all went in.
Pull the Wig Over My Eyes
In the 18th century it was fashionable to wear curly, white wigs. The wigs were called wool, probably because they resembled that of a sheep's wool coat and if the wig got into a person's eyes the couldn't see what was going on.
Ring True or Ring of Truth
A long time ago coins were made of gold, silver and other metals. Sometimes people would mix the metal of their coins with other, less expensive metal... as counterfeit money. When you dropped the coin it would make a particular ringing sound if it was made out of the correct metal. Therefore it would "ring true".
Rule of Thumb
During the beginning of beer making brewers would dip their thumbs into the brew and test the temperature. There was one temperature that was correct for the beer to be done and it was a rule for the beer to reach that temperature or it would be ruined.
Scapegoat
In Bible times a priest would take a goat and lay his hands on it and confess the sins of the people. So all the blame would know lay on the goat, and no longer on the people. The goat would then be set free and would usually be forced to wander off a cliff so the sins would be gone and could not come back to the people.
Short End of the Stick
During the time when people still used candles it was well known that after a candle became too short it would burn out. When people came to visit their hosts would put out long candles so they would burn a good long time. But if the hosts put short candles in the holders it was a sign that they didn't want you to stay long, therefore you would got the "short stick".
Show Your True Colours
A long time ago pirates would change their flags and colours to trick their enemy. If they were captured and there was no hope of escape they would show their enemy their real flags and colours.
Sleep Tight
Back in Colonial times they did not experience the luxury of a spring mattress but instead they tied ropes together to set the other mattress on top of the ropes. Often times these ropes would become loose and the top mattress would slip down and you could fall all the way through them. Keeping the rope tight was important for a goodnight sleep.
Spinster
Originally "spinster" was a woman who made her living by spinning wool on a spinning wheel. Most of the women who had this job were single, because it was the one of the only ways for them to make a living without a husband. Slowly the meaning of "spinster" morphed into meaning "a single woman".
Start from Scratch
A long time ago during the first Olympic games when a race was to be run there was a line scratched in the ground where the race was to begin. So the competitors would have to start from the scratch.
Swashbuckler
Taken Aback
When sailing on the open sea it often happened that the wind would suddenly start moving in the opposite direction taking the ship back. When something goes completely wrong that you were not expecting you are "taken aback".
Turn the Tables
It's been said that in olden days tables would only be finished on one side, so it was less expensive. When families ate alone they would eat on the rough, unfinished side so as not to ruin the nice finished side, but when guests would visit they would turn the "table over".
Wash My Hands Of
This saying was started because of Pontius Pilate when he refused to involve himself in the execution of an innocent man, Jesus. As a symbol of his refusal he washed his hands before the Jews and told them that Jesus' blood was on their heads.
Wear Your Heart on Your Sleeve
Knights in the Middle Ages would wear a token of their lady on their sleeves during a tournament. So saying you "wear your heart on your sleeve" means that you are clearly showing your feelings.
Win or Won Hands Down
During a horse race when a jockey was clearly ahead of everyone else he would relax his hands and put them down at his sides. It's the same as saying you won without a problem and there was really no way you could lose.
Whipping Boy
Prince Edward, before he became King Edward VI, would often be punished for being naughty, but instead of taking the punishment for himself he had a boy that would be whipped for him.

Interesting Blog, and there hangs a tale...
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