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WOW... just wow. These two can't work together as well as I think they do, can they????
Patient Optimist (Trait, Religion):
Benefits: You gain a +2 trait bonus on Diplomacy checks to influence hostile or unfriendly creatures, and if you fail at such an attempt, you may retry it once.
Antagonize (feat):
Benefit: You can make Diplomacy and Intimidate checks to make creatures respond to you with hostility. No matter which skill you use, antagonizing a creature takes a standard action that does not provoke attacks of opportunity, and has a DC equal to 10 + the target’s Hit Dice+ the target’s Wisdom modifier. You cannot make this check against a creature that does not understand you or has an Intelligence score of 3 or lower. Before you make these checks, you may make a Sense Motive check (DC 20) as a swift action to gain an insight bonus on these Diplomacy or Intimidate checks equal to your Charisma bonus until the end of your next turn. The benefits you gain for this check depend on the skill you use. This is a mind-affecting effect.
Diplomacy: You fluster your enemy. For the next minute, the target takes a –2 penalty on all attacks rolls made against creatures other than you and has a 10% spell failure chance on all spells that do not target you or that have you within their area of effect.
Patient Optimist is referring to the Try Again option under Diplomacy:
Try Again: You cannot use Diplomacy to influence a given creature's attitude more than once in a 24-hour period. If a request is refused, the result does not change with additional checks, although other requests might be made. You can retry Diplomacy checks made to gather information.
Since Intimidate can be tried over and over again in anyway (but each retry is more difficult).
Try Again: You can attempt to Intimidate an opponent again, but each additional check increases the DC by +5. This increase resets after 1 hour has passed.
As I understand the "retry" requires a separate standard action since normally (for diplomacy) retries are simply not allowed.
Lets now look at the complete Antagonize:
You can make Diplomacy and Intimidate checks to make creatures respond to you with hostility. No matter which skill you use, antagonizing a creature takes a standard action that does not provoke attacks of opportunity, and has a DC equal to 10 + the target’s Hit Dice + the target’s Wisdom modifier. You cannot make this check against a creature that does not understand you or has an Intelligence score of 3 or lower. Before you make these checks, you may make a Sense Motive check (DC 20) as a swift action to gain an insight bonus on these Diplomacy or Intimidate checks equal to your Charisma bonus until the end of your next turn. The benefits you gain for this check depend on the skill you use. This is a mind-affecting effect.
Diplomacy: You fluster your enemy. For the next minute, the target takes a –2 penalty on all attacks rolls made against creatures other than you and has a 10% spell failure chance on all spells that do not target you or that have you within their area of effect.
Intimidate: The creature flies into a rage. On its next turn, the target must attempt to make a melee attack against you, make a ranged attack against you, target you with a spell, or include you in the area of a spell. The effect ends if the creature is prevented from attacking you or attempting to do so would harm it (for example, if you are on the other side of a chasm or a wall of fire). If it cannot attack you on its turn, you may make the check again as an immediate action to extend the effect for 1 round (but cannot extend it thereafter). The effect ends as soon as the creature attacks you. Once you have targeted a creature with this ability, you cannot target it again for 1 day.
So for the Diplomacy option, if you fail to fluster your opponent you can try to fluster them again with another standard action. If this succeeds you can't use Diplomacy on them for another 24 hours (as normal diplomacy skill). This works.
For the Intimidate, you can try as much as you like until you succeed (taking penalties on each retry), then you can't affect that creature again for 1 day.
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Not entirely correct as it pertains to Antagonize. It uses the Diplomacy and Intimidate skills but it is completely separate from the normal uses of those skills. The Diplomacy part of Antagonize can be used as many times as you want but the Intimidate part can only be used once per creature per day. It says once you have TARGETED the creature, you can't target it again for 1 day so it has nothing to do with success or failure. Then there is the added stipulation that if the target can't attack you (tied up or perhaps under the effects of hold person or something) then you can make one more check to extend it one more round.
As it pertains to the original question, I agree with Avianfoo. I believe Patient Optimist refers to that try again part of the Diplomacy skill.
