Jesus
Why did Jesus cry if he knew he was about to raise Lazarus?
John records this moment with a striking, unusually short sentence: "Jesus wept." What makes it notable is exactly what you've named—he says elsewhere in the same account that he already intends to raise Lazarus, yet he still grieves genuinely alongside Lazarus' family and friends.
The Greek word John uses just before this, describing Jesus as "deeply moved," carries a stronger connotation than simple sadness—closer to a kind of forceful emotional intensity, which some scholars read as including real anger, likely directed at death and suffering itself as intrusions into a world God originally made good, not at the grieving people around him.
Together, these details suggest Jesus' tears weren't performance, and they weren't canceled out by his foreknowledge of the coming miracle. He could grieve real loss and real suffering genuinely, in the moment, even while already planning to reverse this particular instance of it.
Bible quotations in these answers are generally taken from the Christian Standard Bible®, Copyright © 2017 by Holman Bible Publishers. Used by permission. Christian Standard Bible® and CSB® are federally registered trademarks of Holman Bible Publishers. Some biblical wording may be paraphrased or follow other translations.