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Quote image editor Dane C. Ortlund

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“All of our natural intuitions tell us that Jesus is with us, on our side, present and helping, when life is going well. This text says the opposite. It is in "our weaknesses" that Jesus sympathizes with us. The word for "sympathize" here is a compound word formed from the prefix meaning "with" joined with the verb to suffer. "Sympathize" here is not cool and detached pity. It is a depth of felt solidarity such as is echoed in our own lives most closely only as parents to children. Indeed, it is deeper even than that. In our pain, Jesus is pained; in our suffering, he feels the suffering as his own even though it isn't--not that his invincible divinity is threatened, but in the sense that his heart is feelingly drawn into our distress. His human nature engages our troubles comprehensively. His is a love that cannot be held back when he sees his people in pain.” — Dane C. Ortlund

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All of our natural intuitions tell us that Jesus is with us, on our side, present and helping, when life is going well. This text says the opposite. It is in "our weaknesses" that Jesus sympathizes with us. The word for "sympathize" here is a compound word formed from the prefix meaning "with" joined with the verb to suffer. "Sympathize" here is not cool and detached pity. It is a depth of felt solidarity such as is echoed in our own lives most closely only as parents to children. Indeed, it is deeper even than that. In our pain, Jesus is pained; in our suffering, he feels the suffering as his own even though it isn't--not that his invincible divinity is threatened, but in the sense that his heart is feelingly drawn into our distress. His human nature engages our troubles comprehensively. His is a love that cannot be held back when he sees his people in pain.
— Dane C. Ortlund