You say: "Hey that must suck, is there anything I can do to help?" or if you genuinely can't figure it out ask a question about the bit you don't understand: "Let me get this right, someone stole your car and now you're late for a meeting?"

But be careful about asking questions which seem accusatory: "Did you leave your keys in your car? That would be pretty stupid"

Equivalent hypothetical statements in the realm of sexism/discrimination might be: "That sucks, is there anything I can do to help?" or if you're genuinely curious to learn more: "That sounds awful. You've raised some good points, are there any resources I can read so I can further understand?" but don't say: "You weren't wearing those hot-pants were you? That would be pretty stupid"