When praying tarāwīh or tahajjud in the Masjid, a trend that I have noticed is that many people cry during the du’ā in witr. Crying when asking Allāh for something is virtuous and is one of the methods that helps in the acceptance of du’ā, as we are humbling ourselves in front of Allāh and showing our urgent need for His help. However, I would like to point out something which may have been overlooked by some. We stand for (at least) 8 rak’āt in which many verses from the Qur’ān are being recited in front of us before we pray witr, but we don’t end up crying until we pray witr and the imām makes the du’ā?
In the Salāh, the imām is reciting the Qur’ān, which consists of the words of Allāh, and in the du’ā he is supplicating using his own words, yet we seem to be more affected by the words of a man than the words of Allāh. As I said before, it is a good thing to cry before Allāh when asking for something, but do we not feel ashamed to cry before Allāh when asking Him for something whilst we do not cry when the Qur’ān is recited before us? If you are someone that cries when hearing certain verses of the Qur’ān, and cries in witr then alhamdulillāh that is good, but if you are not, then maybe something needs to change.
An example to show what I mean is that a few days ago, I was praying tarāwīh in the Masjid and the imām recited the end of Sūrah Āl-‘Imrān, and throughout the whole salāh I did not hear any crying. When he began making du’ā in the witr salāh, I heard a number of people crying. The reason why I felt something was missing is that the ending of Sūrah Āl-‘Imrān has many powerful verses which implore listeners to contemplate and fear Allāh. It even contains du’ās:
Oh Allāh forgive our sins, and wipe away our wrongdoings. 
Oh Allāh give us what you promised us through your messengers and do not disgrace us on the Day of Judgement. 
These du’ās are very effective ones that should emotionally move a person and cause him or her to cry, yet I heard no cries when the imām recited these verses which are the words of Allāh, but I heard cries when he made du’ā, using the words of man.
I understand many people do not understand Arabic so they say they cannot understand the Qur’ān and therefore are not moved by it. If that is the case then firstly, you should try your best to learn Arabic because you can never appreciate the beauty of the Qur’ān without understanding it in Arabic. Secondly, even if you don’t understand it, you can try and make yourself cry, just like many non-Arabs who I hear crying during the du’ā in witr, which is also in Arabic. Some of the salaf used to say “Cry from the fear of Allāh, and if you don’t cry then forcefully cry.”
One of the reasons for the revelation of the Qur’ān is for it to be contemplated, and Allāh has mentioned this in many verses in the Qur’ān.
A blessed book which We have brought down to you so that they may ponder upon its verses. 
Do they not ponder upon the Qur’ān? 
Do they not ponder upon the Qur’ān? Or do they have locks on their hearts? 
The people of knowledge before it, if its verses are recited to them, they fall on their necks in prostration. And they say, Glory be to our Lord, for His promise was true. And they fall on their necks crying, and it [the Qur’ān] increases them in khushū’ [concentration and humility before their Lord]. 
On the topic of crying, I’m not going to write something really long about the etiquettes of crying, but I just want to remind everyone that when you cry loudly and start wailing, you disturb others around you, and from my limited knowledge, I haven’t come across a narration that the Prophet (peace and blessings be upon him) or his companions used to cry like that. I have only come across narrations of how they used to hide their tears when crying and if they were seen to be crying, then it is just merely heavy breathing or tears tolling down their eyes:
‘Abdullāh b. Mas’ūd recited to the prophet (peace and blessings be upon him) Sūrah al-Nisā’, and when he reached verse 41, the prophet (peace and blessings be upon him) told him to stop, and when he looked up, he saw tears rolling down the Prophet’s (peace and blessings be upon him) blessed face. 
He did not know that the Prophet (peace and blessings be upon him) was crying until he looked at his face.
To conclude, I am not saying it is wrong to cry during the du’ā in witr because it is in fact a good thing to do as it helps in the acceptance of du’ā. What I am saying is that if we find ourselves crying in witr and not during the recitation of the Qur’ān then we need to question our love and connection to the words of Allāh; and if we are neither crying in witr nor during the recitation of the Qur’ān, then we need to question our hearts!
Notes Al-Qur’ān 3:193  Al-Qur’ān 3: 194  Al-Qur’ān 38: 29  Al-Qur’ān 4:82  Al-Qur’ān 47: 24  Al-Qur’ān 17:107-109  Reported in Bukhāri