entristecer

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¿Qué hará eso aparte de entristecerlo?	What's that gonna do but upset the man?
Solo no quería entristecerlo.	I just didn't want to hurt him.
Esta instancia puede dejarlo en un dilema y entristecerlo por perder el acceso a los datos OST de Outlook.	This instance may leave you in dilemma and make you sad for losing access to Outlook OST data.
Piense en una vida en la que jamas nada podria entristecerlo, usted ni siquiera tendria que lamentar la perdida de algo.	Think of a life where nothing would ever make you sad, you wouldn't ever mourn the loss of anything.
De todo esto el señor Pierino no supo nunca nada; para no angustiarlo y entristecerlo le habían ocultado siempre la gravedad de su estado.	Signor Pierino had never known anything of all this; they had always hidden the truth of his condition from him so as not to upset and grieve him.
El daño que Él padece a manos del opresor nunca podrá apenar Su corazón, ni tampoco podrá entristecerlo el ascendiente de quienes han repudiado Su verdad.	The harm He suffereth at the hands of the oppressor can never grieve His heart, nor can He be saddened by the ascendancy of such as have repudiated His truth.