The article discusses the rite of drinking to a fellow symposiast with good wishes and then passing on the same cup to him (προπίνειν); this is comparable, though not identical, to modern toasts. Different variants of this rite are examined (individual toast; toast in the context of the cup passed around among the symposiasts; toast with gift). Special attention is given to the unique usage of προπίνειν in the beginning of Pindar’s Olympian 7, where the poet compares his song in honor of the athlete Diagoras with a golden cup raised by the host in honor of his future son-in¬law and then given to him, full of wine, as a gift in the context of the betrothal ceremony: it is shown that this comparison reflects a real ritual wherein the toast and the subsequent gift of the cup reinforced the alliance between the two families. Typologically close parallels from Lithuanian and Russian folklore suggest that the rite of drinking to future in-laws in order to seal the alliance between two families was an archaic ritual.