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Tear Jerker: Dragon Age: Origins – Awakening
In Awakening, the Warden Keenan explaining that it's too late and his legs are crushed, and all he wants is for his wedding ring to be returned to his wife. If you do take the ring back to Amaranthine, you find out that his wife has been cheating on him.
Almost anything to do with Anders or Justice in Awakenings after playing Dragon Age II. Knowing that no matter what you do, Anders and Justice will merge and leave the Grey Wardens for Kirkwall, even if your epilogue has Anders finding a home with the Wardens. Seeing Vengeance!Anders slowly lose it throughout Dragon Age II is painful, and Justice has been corrupted into Vengeance. Even if your Warden does their best to make all their companions happy and Hawke sides with the mages, Anders will still blow up the Chantry and let you kill him without a fight. The possibility that it is no longer Anders or Justice but Vengeance who controls their actions is unsettling.
And worse, the Warden is indirectly responsible for the Mage-Templar War, after introducing him to Justice, the Grey Wardens philosophy that Utopia Justifies the Means and possibly planting the seeds in his mind with one conversation in particular.
Anders: All I want is a pretty girl, a decent meal, and the right to shoot lightning at fools.
When the darkspawn assault Amaranthine in Awakening, an old man tells you that his family is still in the city and begs you to save them. If you defend the city and defeat the darkspawn generals, the next scene pans over the cheering crowds ... and the corpse of the old man lying in the street while an older woman kneels beside him. It's a reminder that victory has come, but not without cost.
With his Big Screwed-Up Family, it's no wonder that Nathaniel was closer to most of the housekeepers and staff at Vigil's Keep. Upon discovering his surrogate mother figure Adria is one of the people trapped by the darkspawn, he begs you to rescue her, only by the time you discover her, she's already turned into an insane ghoul.
Made worse because we never get to see his reaction or get to comfort him on yet another loss he's suffered.