1)

Was he truly crying?

1.

Radak: He pretended to be crying [Malbim - over an alleged command of Nebuchadnetzar that Gedalyah kill anyone who mourns over Beis Hashem or goes to burn an offering to Hashem there].

2)

Why did he tell them to go to Gedalyah?

1.

Malbim: He wanted people to think that they were killed via Gedalyah's command.

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