Optimistically expects to jump two ways (5)
I believe the answer is:
hopes
'optimistically expects' is the definition.
'hopes' can be an answer for 'expects' ('hope' can be a synonym of 'expect'). I'm not certain of the 'optimistically' bit.
'jump two ways' is the wordplay.
'two ways' can mean two substitutions for 'way'.
'jump' becomes 'hop' (hopping is a kind of jumping).
'way' becomes 'e' (Compass direction - East).
'way' becomes 's' (Compass direction - South).
'hop'+'e'+'s'='HOPES'
'to' is the link.
Can you help me to learn more?
(Other definitions for hopes that I've seen before include "Aspirations, wishes" , "Desires and expects" , "Aspires" , "Expectations" , "Believes that good things may happen" .)