1Frequently; repeatedly; happening often or incessantly.
最近、友達からしきりに連絡が来る。
Lately I've been getting frequent messages from a friend.
会議中にしきりに携帯が鳴って困った。
The phone kept ringing repeatedly during the meeting, which was troublesome.
雨がしきりに降っている。
It keeps raining incessantly.
2Eagerly or intently; used for wanting something strongly or repeatedly urging/requesting.
子供がしきりにアイスをねだる。
The child keeps begging for ice cream.
彼女はしきりに参加したがっていた。
She was very keen to participate.
社長はしきりに意見を求めた。
The president repeatedly asked for opinions.
3Used as an intensifier meaning very; terribly; to a severe degree.
頭がしきりに痛むので病院へ行った。
My head hurt badly, so I went to the hospital.
その出来事が彼をしきりに悩ませた。
That event troubled him greatly.