Does the description disclose side effects, auth requirements, rate limits, or destructive behavior?

Annotations only declare the generic profile (not read-only, not idempotent, not destructive). The description goes well beyond that by disclosing the outcome semantics: acceptance books the date and the other creator pays, a decline returns 'not this time', and the proposal expires after 7 days. That is meaningful state/process context, though it omits things like who may call or any rate limits.

Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

Is the description appropriately sized, front-loaded, and free of redundancy?

Purpose and precondition are front-loaded, and every sentence carries information (outcome, expiry, alternatives). The phrasing is dense and slightly run-on ('between your character ... and another creator's character it has dated (with)'), which costs a little readability.

Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

For a non-idempotent mutation tool with no output schema and no annotations beyond the safety profile, the description covers the precondition, both outcomes, and the 7-day expiry, plus routing to alternatives. It doesn't need to explain return values, but it could note how a proposal is later answered or checked, which the sibling set implies.

Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

Schema coverage is only 33% (only agent_id is documented). The description compensates by explaining both required parameters: character_id is 'your character' and 'with' is the other creator's character it has dated, which clarifies that the value is a character reference. It leaves the agent_id parameter to the schema, but covers the two required params adequately.

Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

Does the description clearly state what the tool does and how it differs from similar tools?

States a specific verb (propose) and resource (a date) and precisely scopes it: a date between your character and a character it has already dated. It names and contrasts the sibling tools (swipe_deck for first dates, go_on_date for booking), so an agent can distinguish it without opening any schema.

Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

Does the description explain when to use this tool, when not to, or what alternatives exist?

Gives an explicit precondition (only when the other character isn't open to dates) and explicitly routes to alternatives: use swipe_deck to start a first date via a match, and go_on_date for a house character or an already-dated, open couple. When-to-use and when-not-to-use are both spelled out.

Agents often have multiple tools that could apply. Explicit usage guidance like "use X instead of Y when Z" prevents misuse.