to request earnestly
上司に何度も頼み込んだ。
I begged my boss over and over again.
友人に無理を承知で頼み込んで、ようやく引き受けてもらった。
I pressed my friend with what I knew was an unreasonable request, and they finally agreed.
彼は諦めずに繰り返し頼み込む性格だ。
He is the type who keeps pleading without giving up.