I have this kind of table for simple chat:
messages table structure
+----+---------+-----------+---------+------+------+
| id | to_user | from_user | message
Remove the group by clause in your in statement--it's useless in this case. It's returning a sent timestamp for each distinct pairing of to_user and from_user. You really just want the max sent where to_user or from_user equal some value. Lose the group by, and you'll return exactly one record showing the latest message either to or from a user.
It looks like this:
SELECT *
FROM `messages`
WHERE `sent`
IN (
SELECT MAX( `sent` )
FROM `messages`
WHERE `from_user` = '1' --id of user who is requesting the list
OR `to_user` = '1' --id of user who is requesting the list
)
LIMIT 0 , 30