Bismillah.
Narrated 'Abdullah bin 'Ubaidullah bin Abi Mulaika:
One of the daughters of 'Uthman died at Mecca. We went to attend her funeral procession. Ibn 'Umar and Ibn Abbas were also present. I sat in between them (or said, I sat beside one of them. Then a man came and sat beside me.) 'Abdullah bin 'Umar said to 'Amr bin 'Uthman, "Will you not prohibit crying as Allah's Apostle has said, 'The dead person is tortured by the crying of his relatives.?" Ibn Abbas said, "Umar used to say so." Then he added narrating, "I accompanied Umar on a journey from Mecca till we reached Al-Baida. There he saw some travelers in the shade of a Samura (A kind of forest tree). He said (to me), "Go and see who those travelers are." So I went and saw that one of them was Suhaib. I told this to 'Umar who then asked me to call him. So I went back to Suhaib and said to him, "Depart and follow the chief of the faithful believers." Later, when 'Umar was stabbed, Suhaib came in weeping and saying, "O my brother, O my friend!" (on this 'Umar said to him), "O Suhaib! Are you weeping for me while the Prophet said, "The dead person is punished by some of the weeping of his relatives?" Ibn Abbas added, "When 'Umar died I told all this to Aisha and she said, 'May Allah be merciful to Umar. By Allah, Allah's Apostle did not say that a believer is punished by the weeping of his relatives. But he said, Allah increases the punishment of a non-believer because of the weeping of his relatives." Aisha further added, "The Quran is sufficient for you (to clear up this point) as Allah has stated: 'No burdened soul will bear another's burden.' " (35.18). Ibn Abbas then said, "Only Allah makes one laugh or cry." Ibn Umar did not say anything after that.
Narrated 'Aisha:
(the wife of the Prophet) Once Allah's Apostle passed by (the grave of) a Jewess whose relatives were weeping over her. He said, "They are weeping over her and she is being tortured in her grave."
Narrated Abu Burda:
That his father said, "When Umar was stabbed, Suhaib started crying: O my brother! 'Umar said, 'Don't you know that the Prophet said: The deceased is tortured for the weeping of the living'?"
Narrated Al-Mughira:
I heard the Prophet saying, "Ascribing false things to me is not like ascribing false things to anyone else. Whosoever tells a lie against me intentionally then surely let him occupy his seat in Hell-Fire." I heard the Prophet saying, "The deceased who is wailed over is tortured for that wailing."
Narrated Ibn 'Umar from his father:
The Prophet said, "The deceased is tortured in his grave for the wailing done over him."
Narrated Shu'ba:
The deceased is tortured for the wailing of the living ones over him.
So? Is the deceased person tormented because of his family's crying for him? What follows is an abridged version of the answer to the question at hand. If you're troubled by the apparent contradiction between the first Hadith on this post and the others, go through this link thoroughly. :)
Shaykh Ibn ‘Uthaymeen (may Allaah have mercy on him) was asked: What is the meaning of the words of the Prophet (peace and blessings of Allaah be upon him): “The believer is tormented because of his family’s crying for him?"
He replied:
What it means is that if his family cries for him, he will know of that and will feel pain. It does not mean that Allaah will punish him for that because Allaah says (interpretation of the meaning): “and no bearer of burdens shall bear the burden of another” [al-An’aam 6:164]. Torment is not necessarily a punishment. Have you not heard the words of the Prophet (peace and blessings of Allaah be upon him), “Travel is a kind of torment”? Travel is not a kind of punishment, but a person suffers torment and exhaustion during it. Similarly, when the deceased person’s family weeps for him, he suffers pain and is upset by that, even though that is not a punishment from Allaah. This interpretation of the hadeeth is quite clear and does not cause any confusion. There is no need to say that this has to do with one who left instructions that they wail for him, or one whose family’s custom was to wail but he did not tell them not to do that. Rather we say that a person may be tormented by something but it doesn’t harm him. End quote.
Majmoo’ Fataawa Ibn ‘Uthaymeen, 17/408
Wassalam.
