I"m interested mainly in Mexican and historicsweetsballroom.com dialects, if that makes a difference, although I"m also interested to know more generally about geographical differences, e.g. in "Narcos" I notice that Escobar"s men refer to him as "Patrón" - is that mainly a Colombian usage ?
The Diccionario de americanismos is a great tool for these kind of questions.
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There you can for example see:
patrón, -na I. 1. m. y f. Ec. Señor, amo. II. 1. adj. Ni. Referido a persona, de pies grandes. ● a. ǁ ~. fórm. Mx, Ho, CR, Ve, Ch, Py; Ur, obsol. Se usa como tratamiento de respeto a alguien. □ a. ǁ ~ de fundo. loc. sust. Ch. Persona que ejerce un poder despótico y arbitrario. pop + cult → espon. b. ǁ ~ de prueba. loc. sust. Cu. Gráfico fijo con líneas y colores que permiten ajustar la imagen de un televisor. c. ǁ ~ grande. loc. sust. Ec. Latifundista o hacendado. rur.
That is, a great set of meanings for patrón depending on the country. Basically (I don"t know if you understand historicsweetsballroom.com) meaning boss, but also other things.
From what I see in the definition, patrón does not have any special meaning in Colombia, so you can go directly to the Dictionary of the RAE and check the word:
patrón, na Del lat. patrōnus; la forma f., del lat. patrōna. 1. m. y f. Defensor, protector. 2. m. y f. Santo titular de una iglesia. 3. m. y f. Santo elegido como protector de un pueblo o congregación religiosa, profesional o civil. 4. m. y f. Dueño de la casa donde alguien se aloja u hospeda. 5. m. y f. señor (‖ persona a la que sirve un criado). 6. m. y f. patrono (‖ persona que emplea trabajadores).
All of them can apply here, since Pablo Escobar was seen as something in between a boss, a saint and a protector among his workers.
This being said,jefe: this is, to me, the most straight-forward way to translate boss. In Spain is the one we use all the time.
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patrón: as indicated above, this word refers to a boss in a work place. In Spain, I hardly ever hear it in colloquial conversations, but (as noted by Nox in comments) it is used to mention the captain of a ship.
So if you want to jokingly call Boss to your girlfriend, I would go for Jefa. Unless you are in some smelly business together and you want to call her capo :)
Bear in mind, though, what DGaleano comments below:
I understand that Mexicans call their mother "la jefa" or "la jefecita"... so please check this out before you get into trouble with your girlfriend. Here a link for that http://www.tubabel.com/definicion/1106 "La patrona" could work better for Mexico