“The naive and guileless are often preyed upon by the shrewd and guileful.”

What is the best definition of guileless?

Check your answer!

Choice A - Incapable of recognizing or telling the truth
Choice B - Marked by artificiality and trickery
Choice C - Lacking beauty and other superficial charms
Choice D - Motivated by honesty and free from artifice


Guileless (adjective) – lacking in or free from deceit or fraudulence; characterized by honesty or innocence  

GRE pro tips:

Attaching the suffix -less to a word denotes a lack of something – in the case of guileless, a lack of guile. But guile isn’t a word you come across every day. It means “deception or deceit” or “artificiality.” So, it makes sense that the adjective guileless means lacking in deceit. It is typically used to describe people who are characterized by honesty and innocence. By contrast, the guileful are characterized by deception and trickery.

Generally, guileless people are incapable of being fake; their motives are pure, and they speak the truth. For example, a naive country guy who moves to the city might be guileless and unsophisticated when he first arrives. This is why guileless people are prime targets for scammers (aka the guileful): it’s not so much that they’re gullible, they just don’t assume impure motives in others, since they are so pure themselves.

Example sentences:

“Scam artists prey upon the most guileless among us – people who lack the sophistication to know a con when they see one.”

“His authentic style of bluegrass and his utterly guileless performance made him stand out in a music industry riddled with phonies and pretenders.”

“When she first moved to New York, Clara too had that guileless expression that characterizes many new arrivals who are still untarnished by city life.”