entristecer

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¿No te entristece un poco que tu matrimonio haya terminado?	Aren't you just a little sad that your marriage is over?
En otras palabras, realmente te entristece lo que hiciste.	In other words, you're truly saddened about what you did.
Cuando luego de festividades solemnes regresas a las actividades ordinarias, te entristece estar de vuelta en la rutina.	When after solemn festivities you turn to ordinary toil, you become struck with the sad everydayness.
¿Por qué te entristece una pequeña cosa dicha contra ti?	Why are you saddened by some little thing said against you?
Ya, ¿pero no te entristece un poco?	Yeah, but doesn't it make you a little sad?
Cariño, ¿te entristece que se él se haya ido?	Sweetheart, are you sad he's gone?
Físicamente, un poco, pero no me digas que te entristece. No es broma.	Physically, a little, but don't tell me that makes you sad.
Luego te enfada, luego te entristece, luego te calma otra vez.	Then makes you angry, then sad, then calm again.
Perdona, solo intentaba aclarar que es lo que te entristece.	I'm sorry, I was just trying to lighten up whatever was making you sad...
¿Qué es lo que te entristece?	What are you saddened about?
¿No te entristece que no compartamos el apellido?	Does it make you kind of sad that we don't share the same last name?
Pero, ¿no te entristece?	But doesn't it make you sad?
¿No te entristece que se vaya?	Are you sad he's leaving?
¿Qué te entristece tanto?	What makes you so sad?
¿No te entristece lastimarte tanto?	Doesn't that make you sad that you've been hurt that much?
¿No te entristece? .	Does that not make you sad?
Esto te entristece mucho.	It makes you very sad.
¿No te entristece ver el fin de un hombre al que una vez llamaste amigo?	The end of one who was once your friend... are you distressed by it?
Si hoy hay algo nuevo que te entristece y que lamentas, di que lo sientes ahora.	And if today there is something new that you rue and regret, say you're sorry now.
¿Eso te entristece, Daniel?	Does that sadden you, Daniel? It intrigues me.