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Is there a specific word for a person who is always concerned with possibilities? For example, they decided to not go to a party with their friends but then wonders what may have happened if they had gone? Or perhaps what would have happened had they not decided to go buy a sandwich and coincidentally meet an old friend at that shop who offered them a much-needed job?

closed as off-topic by MetaEd Sep 11 '17 at 19:55

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    Not a sIngle-word (hence a comment rather than an answer), but there is a phrase living in the subjunctive (mood) – Steve Lovell Jun 11 '17 at 15:05
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    The person is habitually haunted by second thoughts. – Drew Jun 11 '17 at 17:41
  • Defeatist for first example fatalist for second – Kris Jun 11 '17 at 18:23
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    @Drew suggests something close to what i was thinking .. "second guessing yourself" --- "secondguesser" , or "second guessing" without "yourself" means something different. – Tom22 Jun 11 '17 at 22:27
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    the "wistful" emotion is another close possibilitly – Tom22 Jun 12 '17 at 6:47
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"ambivalent" or "feeling ambivalent" ("uncertain of his convictions") seems to fit.

  • ambivalent - (adj) "having or showing ambivalence: ambivalent feelings."

  • from MW - having or showing simultaneous and contradictory attitudes or feelings toward something or someone : characterized by ambivalence.

  • "Americans are deeply ambivalent about the country's foreign role."

  • " Sigmund Freud further developed this definition in his description of ambivalent feelings as the experience of love and hate toward the same object."

Depending on context, "insecure", "diffident", "doubtful" or "unsure" might be more appropriate than "ambivalent".

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How about wistful?

M-W:

wistful: Full of yearning or desire tinged with melancholy

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Ruminator might work; according to Merriam-Webster, to ruminate is "to go over in the mind repeatedly and often casually or slowly."

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Follower ? 2. a person who follows another in regard to his or her ideas or belief. 3. a person who imitates, copies, or takes as a model or ideal. http://www.thefreedictionary.com/follower
"I'm definitely a leader, not a follower."
"I have discovered it's much safer to be a follower."

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