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Considering these, would you please show me what you feel when you are to distinguish between these verbs semantically? I mean eventually what is the difference between challenge and stimulate, with respect to the links and sentences which I have provided?

The MacMillan Dictionary defines stimulating as

  1. making you feel interested

and has the example sentence:
She found her new job challenging and stimulating.

The Free Dictionary entry for challenge includes the definition:

  1. To summon to action, effort, or use; stimulate: a problem that challenges the imagination.

Slovar-vocab.com entry for challenge under section II lists:

3 . SOMETHING DIFFICULT to test the skills or abilities of someone or something SYN stimulate

with the examples:
I’m really at my best when I’m challenged.
challenge somebody to do something
Every teacher ought to be challenging kids to think about current issues.

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  • My first impression: How in the world did he connect those two words?!
    – M.A.R.
    Commented Jul 26, 2015 at 18:48
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    They are two words that mean completely different things. Just look at their antonyms. Challenging is the opposite of easy or simple. Stimulating is the opposite of boring or uninteresting. You've got a lot of definitions here that over-complicate the definition of challenging and imply things that just really aren't part of the definition. Despite what these definitions imply, something can be both challenging but boring. Or easy and stimulating.
    – Catija
    Commented Jul 26, 2015 at 19:36
  • @Catija There are a number of thesauri that relate "stimulating" to "challenging" in the sense of "provocative" (not difficult), so I don't see this question as being way out in left field. thesaurus.com/browse/challenging?s=t
    – ColleenV
    Commented Jul 26, 2015 at 21:42

2 Answers 2

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Your examples are mixing two senses of the word challenging. The entry in Slovar-vocab is wrong when it states "stimulate" is a synonym of "challenge" when it means "something difficult".

  1. The book I read stimulated me.
  2. The book I read challenged me.

In sentence 1, the book is thought provoking or inspired interest in a topic.
In sentence 2, the language of the book was difficult and it took a lot of effort to read, or it forced me to confront my thinking about something and it was a little uncomfortable for me to realize that maybe I need to change my opinion or understanding. It's not clear from the context which meaning is the intended one.

One interesting thing to note is that while "stimulating" is sometimes listed as a synonym for "challenging", the opposite isn't usually true. They are only related through the word "provocative" which has two meanings:

  1. Serving or tending to elicit a strong, often negative sentiment in another person; exasperating.
  2. Serving or tending to excite, stimulate or arouse sexual interest.

"Stimulating" is provocative in a positive sense, but without necessarily the sexual connotation, like "exciting". "Challenging" can mean provocative in a negative sense, like "defiant" or "disturbing", but it usually means "difficult to do".

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  • Note also that "challenging" is often used without a negative connotation, for example "I like to challenge my students by giving them problems to solve that they would not have encountered before", but I see what you mean. +1 for the amazing answer.
    – 13509
    Commented Jul 27, 2015 at 13:59
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    @parkgatedev You're right that challenge isn't always negative. I'm troubled by the dictionaries that are connecting "challenge" the verb with "provoke". I may rewrite this answer after I've consulted some other sources. Challenge to me is "stimulate by presenting something difficult", and I think let "challenging" lead me out into the weeds a bit.
    – ColleenV
    Commented Jul 27, 2015 at 14:29
  • You're absolutely correct, I was just checking that you would include both sides in your answer.
    – 13509
    Commented Jul 27, 2015 at 15:18
  • Challenge is related to provoke in the original sense of the word challenge "a call or summons to engage in any contest, as of skill, strength", as in "I challenge you to a duel." In that case, I would be "provoking" you to fight.
    – TBridges42
    Commented Jul 29, 2015 at 20:01
  • @TBridges42 Sure, but challenging you to a duel is not provoking you in the same way that stimulating you by offering you a brain teaser is... the connection there bothers me and I've been pondering how to explain it clearly. I don't think stimulate is connected with provoke in the same sense that challenge is.
    – ColleenV
    Commented Jul 29, 2015 at 20:50
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The only overlap between stimulating and challenging is in how some people feel or respond when challenged. Some people shy away from challenges; some find being challenged stimulating or provoking.

Doing certain things can be challenging or difficult for some people.

With her sprained ankle, she found climbing the stairs challenging.

A person can challenge another person by making things difficult for them or obstructing them:

The guard at the desk challenged the visitor to show some proof of identity.

A person can challenge another person by being their adversary:

I challenge you to a game of chess. You be white. I will attempt to obstruct you with every move I make.

An activity can be difficult to master:

Chess is a challenging game.

Some people become stimulated or interested when their minds are challenged.

Solving a challenging math problem is for him very stimulating.

Some people can feel provoked to action by a difficult task:

The mountaineers saw the sheer rock face as a challenge to their abilities and felt compelled to attempt an ascent.

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