~きり (since)
Nothing has happened since one last event
You’ll be able to mark a past action as the last occurrence before a continuing absence or unchanged situation.

おじいちゃんは、昔の友達と十年前に会ったきり、一度も会っていません。
ojiichan wa, mukashi no tomodachi to juunen mae ni atta kiri, ichido mo atte imasen.
What do you think this sentence means?
Grandpa hasn't seen his old friend once since they met ten years ago.
Not since that last time
Past plain form + きり means that the first event was the last time it happened, and nothing similar has happened since. It often appears with a continuing negative meaning that is understood from context.
父は今朝出かけたきり、まだ帰ってきません。
chichi wa kesa dekaketa kiri, mada kaette kimasen.
My father went out this morning and still has not come back.
その店には一度行ったきりです。
sono mise ni wa ichido itta kiri desu.
I have only been to that shop once.
Use a past event as the last one
Attach きり to a past plain verb. Follow it with a continuing negative or unchanged situation, or end with です when the absence is clear.
朝食を食べたきりです。
choushoku o tabeta kiri desu.
I have eaten nothing since breakfast.
兄は東京の大学に入ったきり、ほとんど家に帰ってこない。
ani wa toukyou no daigaku ni haitta kiri, hotondo ie ni kaette konai.
Ever since my older brother started university in Tokyo, he hardly ever comes home.
高校を卒業したきり、担任の先生には会っていません。
koukou o sotsugyou shita kiri, tannin no sensei ni wa atte imasen.
I haven’t seen my homeroom teacher since I graduated from high school.
祖母は先月入院したきり、まだ退院できていません。
sobo wa sengetsu nyuuin shita kiri, mada taiin dekite imasen.
My grandmother went into the hospital last month and still hasn’t been able to leave.
7 more examples in the grammar path — free for a limited time.