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упрашивать

to beg, to plead with

ʊ p r a ʂ ɨ v ə tʲ
у away or off; often marks a completed action + прашив to beg, to plead with + ать Infinitive
verb Rare #52,385
to beg, to plead with Suggests persistent or repeated asking.
RU: Не нужно меня упрашивать.
EN: You don't have to keep asking me.

Не заставляйте меня упрашивать вас.

Don't make me beg you.

— Ночи Кабирии (1957)

Мне пришлось упрашивать своих друзей, чтобы они пришли.

I had to beg my friends to come.

Вы будете меня упрашивать?

Are you going to beg me?

Упрашивать меня не пришлось.

You didn't have to persuade me.

Sounds similar to

спрашивать s p r a ʂ ɨ v ə tʲ