estar entre Pinto y Valdemoro

Literally, “be between Pinto and Valdemoro”. Pinto and Valdemoro are two towns in the province of Madrid that used to be divided by a stream. The popular etymology is that once upon a time, a drunk man was walking along the river, jumping from one bank to the other and saying he was in Pinto, then Valdemoro, then Pinto, then Valdemoro again. After a while, he fell into the stream and then announced he was “between Pinto and Valdemoro”.[1] Other versions of the etymology allude to the kings of the House of Habsburg, who were said to be “between Pinto and Valdemoro” when frequenting a whorehouse between the two towns. Yet another version refers to wines. Valdemoro was famed for being of the highest quality in the land, whereas that of Pinto was a lower quality; thus a wine that was “between Pinto and Valdemoro” was one of mediocre quality.[2]

estar entre Pinto y Valdemoro

1. (idiomatic, Spain) in two minds, undecided
2. (colloquial, Spain, idiomatic) to be half gone, to be three sheets to the wind[3]

• “estar alguien entre Pinto y Valdemoro”, in Diccionario de la lengua española, Vigésima tercera edición, Real Academia Española, 2014