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Example 1

I was a generous kid. I shared my toys with my friends if/when/whenever I bought new ones.

Do all three of if, when, and whenever result in the same meaning: that it was a past reoccurring thing?

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    Does this answer your question? When are 'if' and 'when' interchangeable? In your example text, if and when are equivalent, and the only difference is that whenever is a bit more "emphatic" (whatever that means in the specific context! :) Some people might think if is somewhat less emphatic (implying that new toys were bought less often than with when, whenever). Commented May 30 at 17:04
  • In the past decade or so I've noticed that certain speakers (of American English) often use whenever as synonymous with when. In my own dialect, one would never say for instance *whenever I was in high school unless either (1) there were several non-contiguous periods of being in high school and every one of them is being referred to or (2) one has forgotten in which period of time the being in high school took place. Commented May 30 at 17:13
  • I was a generous kid. I shared my toys with my friends if/when/whenever my parents bought me new ones.
    – Lambie
    Commented May 30 at 17:44
  • Is there a difference between when and whenever? Yes. whenever has built-in emphasis. The logical factual outcome may have been the same but meaning involves more than fact; it involves the speaker's attitude towards the utterance, their emotional involvement in it.
    – TimR
    Commented May 30 at 20:13

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Basically, yes. The 'if' means that the kid may or may not have gotten any toys. 'When' implies that they did. 'Whenever' implies that every time they got a toy they shared it without fail. But in this case basically they're the same.

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