importune
UK: /ɪmˈpɔːtjuːn/ | US: /ɪmˈpɔːrtuːn/
vt. to persistently ask or demand something in an annoying or troublesome way
vt. to beg or solicit urgently or pressingly
adj. (archaic) troublesome; persistent in solicitation
The word "importune" traces back to Latin "importunus," meaning "inconvenient, troublesome," originally referring to a lack of favorable wind for sailing (from "in-" + "portus," harbor). Over time, it evolved to describe persistent or untimely demands, reflecting the idea of "forcing an opportunity" regardless of appropriateness.
The salesman continued to importune the customer despite her clear disinterest.
Refugees importuned the embassy for visas, desperate to escape the war.
His importune requests for favors strained their friendship.
She felt guilty but had to importune her boss for an advance on her salary.
The beggar importuned passersby with relentless pleas for money.