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I was just wondering, I know somebody here knows what word I'm referring to.
For example:

Person 1: I like that guy because of his looks.

Person 2: Do you really? Or are you just feeling lonely?

Person 1: Geez, you are such a "word".

closed as off-topic by sumelic, Centaurus, Nathaniel, Drew, tchrist May 2 '16 at 2:03

This question appears to be off-topic. The users who voted to close gave this specific reason:

  • "Questions on choosing an ideal word or phrase must include information on how it will be used in order to be answered. For help writing a good word or phrase request, see: About single word requests" – sumelic, Nathaniel, Drew
If this question can be reworded to fit the rules in the help center, please edit the question.

  • Whatever the word is, the person is from Missouri. – Drew May 1 '16 at 23:55
  • Thanks for the edit. The current example sentence suggests that you want a noun. Many of the answers (including the accepted answer) are adjectives, though. Do you care, or is either OK? – sumelic May 2 '16 at 3:35
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    The title is contradictory to the example given. But regardless of that, the selected answer (ambivalent) does not fit either description. First, the word should be a noun to fit in the example sentence, otherwise you need two: e.g. You're such an ambivalent person Secondly, ambivalent (simultaneous and contradictory attitudes or feelings) does not mean someone who doesn't believe what they hear, and/or second guesses everything. IMO "a cynic" could fit the example, but not with the title – Mari-Lou A May 2 '16 at 8:13
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    @Mari-LouA I see, I agree with everything you said. I also think the best word that describes my example is "cynic". Thank you for all your help and I apologize for the slight difference of my example and my description. – Jane Doe May 2 '16 at 15:23
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Try skeptic

A skeptic always doubts and from that I'm sure that he'll second guess pretty much everything, though not exclusively mentioned in the definition.

  • If you're looking for a noun(you didn't specify), there's also "doubting thomas" idiom for such a person. – user143977 May 1 '16 at 16:39
  • @Jakub the beauty of sharing: learn something from that experience. Great new addition to my vocabulary. – vickyace May 1 '16 at 16:45
  • That's the word I'm looking for. – Jane Doe May 1 '16 at 16:45
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    I have to disagree with this... this may well be the word you're groping for, but it doesn't mean what you asked for initially. A sceptic/skeptic does not second-guess things; they merely doubt things and don't take things at face value. I suspect you're crossing from the "doubting Thomas" territory into the land of "know-all"/"smart alec". That's not the same at all. – Prof Yaffle May 1 '16 at 16:55
  • @ProfYaffle I see, I suppose you are correct but seeing I've just replied "that's the word I'm looking for" would contradict this statement however I am open for other possible words that fit better with my description. If you do know, please tell me. – Jane Doe May 1 '16 at 17:44
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wishy-washy, as defined by The Free Dictionary:

Irresolute or indecisive: a wishy-washy supervisor who can't decide what to do.

Lacking in purpose; weak or ineffective: a wishy-washy response to the criticism

yourdictionary.com has this definition and a good example:

The definition of wishy washy is someone or something uncertain, indecisive and wavering, or someone who cannot make up his mind.

An example of a wishy washy person is someone who says yes to an invitation, and then no, and then that he will think about it

  • Similarly, "Milquetoast" - someone who is overly sensitive, timid, indecisive or cowardly. Based on a cartoon character, Caspar Milquetoast, popular in America in the 1920's. – pepper May 2 '16 at 6:36
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Bluffer

This is another sort of person who makes guesses if he/she doesn't exactly know the answer. This person is "doubtful" in a totally different way.

A bluffer is someone who bluffs

Bluff (verb) Oxford Dictionary

Try to deceive someone as to one’s abilities or intentions:

(bluff it out) Survive a difficult situation by maintaining a pretence.

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If you want some pedantic equivalent to "skeptic", consider pyrrhonic (or "pyrrhonian").

Pyrrho was a Greek philosopher, founder of scepticism. He maintained that true wisdom and happiness lie in suspension of judgment, since certain knowledge is impossible to attain.

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A person who has trouble making decisions is indecisive:

: not able to make choices quickly and confidently

: not settling something or making something final or certain

[Merriam-Webster]

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Ambivalent, from Latin ambi- "both" + valentia "strength"

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Reluctant, I believe.

I considered skeptic but a skeptic doesnt necessarily harbor any doubts, they just cannot be sure. Remember that sure and doubting are not polar as they are complementary and that they represent a hindered state towards certainty in either direction. Or something like that.

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