The Casanova Cave kit features a magazine promoting a high-end watch, which Don Lothario appears to own, as it's one of his CAS items in the same kit!
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IF: You learn a specific Olive Specter rumor
THEN: Layne's available rumors change
AND: If you befriend him
AND: Get his new rumor
THEN: He calls you
AND: Your answer unlocks an interaction
THEN: You can use it on him
WHICH: CHANGES ONE OF HIS TRAITS!