3e SRD:Intimidate Skill
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The character can change others' behavior with a successful check. The DC is typically 10 + the target's Hit Dice. Any bonuses that a target may have on saving throws against fear increase the DC.
Generally, retries do not work. Even if the initial check succeeds, the other character can only be intimidated so far, and a retry doesn't help. If the initial check fails, the other character has probably become more firmly resolved to resist the intimidator, and a retry is futile.
If the character has 5 or more ranks in Bluff, the character gets a +2 synergy bonus on Intimidate checks.