1. Approach
   Aberration
2. Ingress
   Arrival

"Aberration" first appeared in the 1590s to mean "a wandering" or "a straying." The word comes from Latin "aberrationem," which means "a wandering."

1. Callow
   Ripened
2. Matured
   Mellow

"Callow" is derived from the Old English word "calu," which means "bare" or "bald." The word was first used in the year 1580.

1. Voluminous
   Insular
2. Broad
   Impartial

"Insular" was first used in 1611 to mean "relating to an island." The word comes from Latin "insula," which means "island."

1. Approbate
   Sanction
2. Ratify
   Flout

"Flout" appeared as a verb in the 1550s to mean "to scorn." Its origin is likely from the Middle English word "flouten," which means "to play the flute."

1. Douceur
   Largess
2. Treasure
   Cultivate

"Largess" is a 13th-century word that meant "generosity" at the time. That definition still stands, and its meaning also includes "a liberal giving of money or gifts to someone is or who is perceived as inferior."

1. Maudlin
   Cynical
2. Misanthropic
   Pessimistic

"Maudlin" implies insincere emotion that's due to blatant insincerity or emotional impairment, as if drunken. "Maudlin" is a variation of "Mary Magdalene," who is widely perceived as an emotional, repentant sinner.

1. Rebuff
   Banish
2. Acquiesce
   Ostracize

"Acquiesce" is a word from the 1610s and is derived from the Latin "acquiescere," which means "to become quiet" or "to remain at rest," which implies "satisfaction." The word's first and existing meaning is "implicit submission and compliance."

1. Artifcial
   Verisimilitude
2. Delusory
   Specious

"Verisimilitude" is "the state of seeming true or real." The prefix "veri-" is from Latin "verus," which means "true or genuine." "Verisimilitude" first appeared in the 1570s to mean "the quality or state of being true."

1. Countenance
   Inveigh
2. Demean
   Repose

"Inveigh" is a 1520s word that means "to speak or write about something in a tremendously hostile manner." "Declaim" is similar in meaning, but the synonym further implies "making impassioned rhetoric as if to an audience."

1. Sanctimonious
   Artless
2. Brusque
   Veracious

"Sanctimonious" describes "deliberately making a show of being morally superior to others." The word first appeared around the year 1600.

1. Standpat
   Blimpish
2. Histrionic
   Modern

"Histrionic" was first used in 1648 to mean "willfully affected." The word is derived from the Latin "histrionicus," which means "concerning an actor."

1. Demure
   Impertinent
2. Coquettish
   Governessy

"Impertinent" also means "rude" and "arrogant." The term first appeared in the late 14th century to mean "irrelevant." "Impertinent" is derived from the Old French "impertinent," which means "not belonging" or "not to the point."

1. Foolhardy
   Audacious
2. Circumspect
   Impetuous

"Circumspect" is an adjective that means "carefully considering potential consequences, and to avoid risk." "Circumspect" first appeared in the early 15th century and is derived from the Latin "circumspectus," which means "guarded," "intentional" and "well-considered."

1. Sufferance
   Sanction
2. Tolerance
   Dictum

"Dictum" was first used in 1586 to mean "a formal pronouncement" or "notable statement." The word's Latin meaning is "prophecy, proverb" or "an order."

1. Replumb
   Connive
2. Fathom
   Authenticate

"Connive" is from the Latin "connivere," meaning "to wink." The word first appeared in 1601 to mean "to pretend ignorance" or "fail to address that which one should oppose."

1. Incurious
   Flabbergasted
2. Impervious
   Listless

"Flabbergasted" is the past participle form of the verb "flabbergast." "Flabbergasted" first appeared as a trendy word in a 1772 magazine article. "Amazed," "astounded" and "dumbfounded" are related words.

1. Banausic
   Abortive
2. Frivolous
   Fitting

"Abortive" is an adjective that means "failing to accomplish an intended result." "Abortive" is a 15th-century word that was first used to mean "prematurely born."

1. Mawkish
   Poignant
2. Mordant
   Insipid

"Dull" or "uninteresting" are synonyms for "insipid," which was first used in the 1610s to mean "without taste." "Insipid" is derived from the Late Latin "inspidus," which means "tasteless."

1. Buoyant
   Winsome
2. Insouciant
   Lugubrious

"Lugubrious" implies an exaggerated mournful state. The word was first used in 1585 to mean "mournful." "Dismal" and "melancholy" are related terms.

1. Putative
   Demonstrable
2. Arcane
   Empirical

"Arcane" means "understood by select few," "mysterious" and "esoteric." "Arcane" first appeared in the 1540s and is derived from the Latin "arcanus," which means "concealed" or "private."

1. Adjoining or touching
   Intimate
2. Clandestine
   Impenetrable

The adjective "contiguous" comes from the Latin "contiguus," which means "touching," "near" or "bordering upon." "Contiguous" was first used in the early 1600s to mean "in actual contact with."

1. Merit
   Turpitude
2. Probity
   Scrupulosity

"Turpitude" is a noun that is synonymous with "depravity." "Turpitude" first appeared in the 15th century to mean "innate evil."

1. Agog
   Munificent
2. Apathetic
   Malicious

"Munificent" first appeared in the year 1565 to mean "lavish giving." The word is derived from the Latin "munificus," which means "liberal" and "bountiful."

1. Chivalrous
   Peremptory
2. Dutiful
   Demure

"Peremptory" means "authoritative" and "abrupt"; "arrogant" is a related term. "Peremptory" was first used as a legal term in the mid-15th century to mean "precluding a right of action."

1. Placative
   Sanguine
2. Dulling
   Piercing

"Sanguine" implies "confident optimism." The word first appeared in the 14th century as an adjective to mean "blood-red." In the 15th century, it was used as a noun to define a "moderate to saturated tone of red."

1. Piousness
   Devotion
2. Dubiousness
   Perfidy

"Perfidy" is a noun that also implies "untrustworthiness." "Perfidy" was first used in 1592 to mean "a state of being disloyal or faithless." The Latin term "perfidia," meaning "falsehood" or "faithlessness," precedes "perfidy."

1. Perspicuous
   Luculent
2. Abstruse
   Elephantine

"Abstruse" first appeared in 1549 to mean "difficult to understand." The word is derived from the Latin "abstrusus," which means "concealed."

1. Conciliate
   Estrange
2. Cadge
   Envenom

The verb "cadge" implies that one is not entitled to receive what is requested or obtained. The noun "cadge" is used in falconry and is "a padded wooden frame used to transport hooded hawks to a field."

1. Vigorous
   Flimsy
2. Thickish
   Glutinous

"Tenuous" first appeared in the year 1597 to mean "not compact." The word is derived from the Latin "tenuis," which means "thin." "Delicate" and "insubstantial" are related terms.

1. Vitiate
   Meliorate
2. Ennoble
   Ensky

The Latin word "vitiatus" precedes "vitiate," which was first used in the year 1534 as a transitive verb to mean "to make faulty or defective." "Vitiate" also means "to debase morally."

1. Obstreperous
   Repressed
2. Unpretentious
   Pulchritude

"Obstreperous" is an adjective used around the start of the 17th century to mean "marked by particularly unruly noisiness." "Obstreperous" is derived from the Latin "obstreperus," which means "clamorous."

1. Artless
   Echt
2. Unctuous
   Malodorous

A more conventional definition of "unctuous" is "ingratiatingly flattering," which also implies unpleasantness. "Unctuous" is a 15th-century word that was first used to mean "oily."

1. Slavish
   Factitious
2. Mimetic
   Contumacious

"Contumacious" is "stubbornness" to the point of rebelliousness. "Contumacious" was first used in this fashion in the year 1583. Other new words from the same year include "generous" and "pertinacious."

1. Choppy
   Rudimentary
2. Newfangled
   Unremitting

"Unremitting" is an adjective that was first used in 1670 to mean "constant." The prefix "un-" means "not"; "remitting" is the present particle form of "remit," which means to "send back," "restore," "subside" or "refrain."

1. Decipher
   Intuit
2. Obfuscate
   Conjecture

"Complicate," "baffle" and "befuddle" are synonyms for "obfuscate," which first appeared in the year 1536 as a transitive verb to mean "to throw into shadow." In the intransitive sense, "obfuscate" means "to be unclear or evasive."