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As someone who's gone through a lot of tragedy in my 30+ years on this planet it usuall goes like this.
The time leading up to is generally a sad one, the actual day is quite heavy, lots of crying, maybe anger, usual 5 stages of grief, now you think you're done crying but you ain't, you're reacting to what is happening, but in a few weeks you'll think "boy I really wanna see so and so again", then it hits you, you can't, they're gone, just their memories remain.
THEN it really hits you and you probably cry the hardest.
If its sudden, say they just graduate with no fanfare/they die, its a similar phase, but the initial shock is the hardest, just constant questions, anger over what happened, then what settles is things left undone, shit you wanted to see.
Far as pain goes, it really depends on what it meant to you, most pain you simply learn to live with, after awhile it kind of fades, something you'll be reminded off it here and there, the longer time passes the more it slips away from you, sometimes you don't even remember when they passed because its been so long.