I'm not even sure if this is possible but I'm trying to do different UPDATE if a certain condition is met.
user [id, start_date(NOT NULL), end_date(NULL), reason(NULL), .....]
user_roles [id, role_id, user_id, start_date(NOT NULL), end_date(NULL)]
What I have right now is this but this only works if a role exists for the user and it's end_date is NULL:
UPDATE user p 
JOIN user_roles ur ON p.id = ur.user_id 
SET ur.end_date = NOW()
   , p.end_date = NOW()
   , p.reason = "Retired" 
WHERE p.id = 5 
AND ur.end_date IS NULL
I was thinking of doing something like this:
IF EXISTS (SELECT id FROM user_roles 
WHERE user_id = 5 AND end_date IS NULL)
THEN 
    UPDATE user p 
    JOIN user_roles ur ON p.id = ur.user_id 
    SET ur.end_date = NOW()
        , p.end_date = NOW()
        , p.reason = "Retired" 
    WHERE p.id = 5 AND ur.end_date IS NULL 
ELSE 
    UPDATE user 
    SET end_date = NOW()
        , reason = "Retired" 
    WHERE id = 5 
END IF
                Since the only difference is whether you are setting ur.end_Date to either the current Date or setting it to it's existing date could you not just use the following:
UPDATE user p  
JOIN user_roles ur 
ON p.id = ur.user_id  
SET 
ur.end_date = IF (ur.end_date IS NULL, NOW(), ur.end_date),
p.end_date = NOW(), 
p.reason = "Retired" 
WHERE p.id = 5
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