He approaches one side then the other (2-7)

I believe the answer is:

go-between

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'he approaches' is the definition.
The answer is a person as well as being a singular noun. This is suggested by the definition.

'one side then the other' is the wordplay.
'one side' indicates taking half.
'then' becomes 'ergo' (therefore).
'the other' becomes 'between' (I can't justify this - if you can you should believe this answer much more).
'ergo' halved is 'go'.
'go'+'between'='GO-BETWEEN'

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(Other definitions for go-between that I've seen before include "One who acts as messenger or negotiator" , "Runner" , "Intermediary" .)

I've seen this clue in The Globe and Mail.

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