Frequently out of date (8)
I believe the answer is:
ofttimes
'frequently' is the definition.
(I know that frequently can be written as ofttimes)
'of date' is the wordplay.
I cannot really see how this works, but
'of' could be 'o' and 'o' is located in the answer.
'date' could be 'time' (period of time) and 'time' is present in the answer.
This explanation may well be incorrect...
'out' is the link.
Can you help me to learn more?
(Another definition for ofttimes that I've seen is " Frequently, at short intervals (arch/poetic)".)