Ah. What happens is that you still get the first match in the string. In this case, that's the match starting at "<samp>wants VB</samp>" (what's the `*' doing after `VB)' in your regexp, anyway?). You could use greediness to hit the last match in the string:

$sentence =~ /.*(\w+\sVB)(.|\n)*?($phrase)/
[download]

But that still doesn't guarantee "closenessest", just "lastness".

Your alternative is to look up and use sexegers for this second task. You will find much information on this very site...

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PS. Please try to format your writeups so we can read them...