YOU SAID:

when a woman tenses up upon encountering a shabbily dressed man on a dark street late at night,

INTO JAPANESE

深夜の暗い道でみすぼらしい服装の男に遭遇して女性が緊張したとき、

BACK INTO ENGLISH

When a woman gets nervous when she encounters a poorly dressed man on a dark street late at night,

INTO JAPANESE

深夜の暗い道で、服装の悪い男性に遭遇して女性が緊張すると、

BACK INTO ENGLISH

When a woman gets nervous when she encounters a poorly dressed man on a dark street late at night,