A chap to try out with hesitation? (5)
I believe the answer is:
terry
'a chap' is the definition.
'try out with hesitation?' is the wordplay.
'try out' becomes 'try' ('try' can be a synonym of 'try out').
'with' indicates putting letters inside.
'hesitation?' becomes 'er'.
'try' enclosing 'er' is 'TERRY'.
'to' is the link.
(Other definitions for terry that I've seen before include "Loop of pile fabric; England footballer" , "Terence (dim.)" , "Towelling material" , "Famous actress" , "A man" .)