The Meaning of Endearment
Tawaddud linguistically: comes from wudd. It is love that leads to all entries of good.  Lisan al-`Arab, Ibn Manzur (3/453).
Tawaddud technically: is seeking another’s love depending on the respective need.  al-Ta`rifat, al-Jurjani (p. 71); Mu`jam Maqalid al-`Ulum, al-Suyuti (p. 208). It is also said that tawaddud is affirming ties which bring about love.  Fath al-Bari, Ibn Hajar (10/439). The Difference between Endearment, Affection (Ta`atuf), Compassion (Tarahum), and Love (Hubb)
Compassion is to have mercy with one another due to the brotherhood of faith, nothing else. Endearment is affirming ties which bring about love, like visiting one another and giving gifts. As for affection, it is to help one another, just as one does `atf of a cloak on oneself to strengthen one. Love is that which is brought about through inherent disposition as well as wisdom, both of them. Endearment is solely brought about through one’s disposition.Commandments of Endearment and Encouragement towards it in the Qur’an and Sunnah
❖ Allah, exalted, says: “Repel evil with what is better and your enemy will become as close as an old and valued friend.” Fussilat: 34.
❖ He also says, exalted: “Another of His signs is that He created spouses from among yourselves for you to live with in tranquility: He ordained love and mercy between you. There truly are signs in this for those who reflect.” al-Rum: 21. Meaning, He ordained marital relations between you as a means of love that you exercise endearment through, and maintain ties between one another due to.
❖ He, exalted, also says: “Surely, the Lord of Mercy will give love to those who believe and do righteous deeds.” Maryam: 96. Meaning, he will love them and place love for them among the believers.  Tafsir Mujahid (p. 459).
❖ al-Nu`man ibn Bashir, Allah be pleased with them both, said: “The Messenger of Allah ﷺ said: ‘The example of the believers in their endearment, compassion, and affection to one another is that of a body: if a part of it is in distress, the rest of the body is feverish and unable to rest.’”  Reported by al-Bukhari (6011) and Muslim (2586), and the wording is his.
❖ Abu Hurayrah, Allah be pleased with him, narrates that a man said: “Messenger of Allah, I have family with whom I try to maintain ties, but they cut them off with me. I am beneficent to them, but they are maleficent with me. I am forbearing with them, and they are ignorant in treating me.” He ﷺ replied: “If they are as you said, then it is like you are throwing hot ashes at them. Allah will remain as your supporter as long as you remain upon what you are doing.”  Reported by Muslim (2558). Quotes of the Scholars and Predecessors in Praising Endearment
❖ al-Hasan said: “Appreciation is half of gain, endearment is half of rationality, and asking well is half of knowledge.”  al-Bayan wa al-Tabyin, al-Jahiz (2/65).
❖ Maymun ibn Mihran said: “Decency is being bright-faced, endearing to people, and fulfilling their needs.”  Muru’ah, Ibn Razban (p. 70). Types of Endearment to People
Endearment is of two types: Praiseworthy endearment: that is moderate love for those of virtue, nobility, dignity, and status - those who excel among people. Blameworthy endearment: that is seeking the love and affection of the lowly and depraved among people, and seeking the endearment of women, and those of lewdness.
Benefits of Endearment to People
It is a means for love and sociability, and strengthens relations among people. Endearment and strengthening ties of affection among people is the basis for building a strong society founded on aiding and caring for one another. Endearment reflects spiritual beauty and virtuous morality which Islam came to perfect and emphasise. Endearment to people and gaining their love and trust facilitates their accepting what you give and call towards with ease and relatively less effort. Endearment is a way to remove animosity and hate, leading to pure hearts.
Forms of Endearment to People
Good morals with pleasantness is the key to people’s hearts and what incites their love. It prepares a place for one in the hearts of others. Overlooking others’ mistakes, and not highlighting every single fault and shortcoming one’s companion falls into. Gentleness and being soft and lenient. Seeking what is easy and being easy-going in treating others is a way to be endearing to them. Relieving the difficulties of brothers. Standing by their side in strenuous and sad times, consoling them and being good to them throughout, are all means to endearment to them. Often visiting each other and asking about each other, avoiding not being in contact with those seeking endearment of one another. Revering the old, and being compassionate with the young.
Barriers to Acquiring Endearment to the People
Arrogance and haughtiness. Frowning and being stern-faced with people. Being harsh with one’s words, explicit in speech, and obscene in imagery. Stinginess and miserliness. Being harsh in nature, and stern in others’ treatment. Differences which cause animosity and hostility are a barrier to having endearment and sociability in society. Examples of Endearment from the Life of the Prophet ﷺ, Companions, Righteous Predecessors, and Scholars
❖ He ﷺ would be endearing to his companions and supplicating for them. Jarir, Allah be pleased with him, said: “The Prophet ﷺ never made a barrier between him and me since I became Muslim. He never saw me but he smiled at me. I complained to him once that I am unable to be firm in horse riding, so he struck my chest and said: “Allah, keep him firm, and make him guided, a guide for others.”  Reported by al-Bukhari (3035, 3036) and this is his wording, as well as Muslim (2475).
❖ The companions were also keen to be characterised with this attribute - that they are loved by the people - like when Abu Hurayrah came to the Prophet ﷺ asking him to supplicate to Allah for him and his mother that they become beloved to the believers, and the believers are made beloved to them. Abu Hurayrah, Allah be pleased with him, said: “I said: ‘Messenger of Allah, supplicate to Allah for me and my mother that he makes us beloved to the believers, and makes the believers beloved to us.’ The Messenger of Allah ﷺ said: ‘Allah, make this young slave of yours - meaning, Abu Hurayrah - and his mother beloved to Your believing slaves, and make the believers beloved to them.’ Since then, there was not a believer that Allah created who hears about me except that he loved me.”  Reported by Muslim (2391).
❖ Ibn Kathir said in his biography of Ibn Qayyim al-Jawziyyah, Allah have mercy upon him: “He used to be well-read with good character, very endearing, not harming anyone nor envying them. He did not mock or hate anyone.”  al-Bidayah wa al-Nihayah, Ibn Kathir (14/270).
❖ It is found in the biography of Muhammad ibn Ibrahim ibn `Abd al-Rahman al-Sulami al-Munawi, then al-Qahiri, that: “he was very endearing to the people, held in high regards among them generally and specifically, beloved to them.”  Inba’ al-Ghumr bi-Abna’ al-`Umr, Ibn Hajar (2/181). Quotes in Endearment
❖ It was said to `Abd al-Malik ibn Marwan: “What did you gain in this kingship of yours?” He replied: “The endearment of men.”  Adab al-Dunya wa al-Din, al-Mawardi (p. 181).
❖ It is narrated that Luqman said to his son: “My son, be endearing to the people, for endearment to them is security, and being hostile to them is fear.”  Nathr al-Durr fi al-Muhadarat, al-Abi (7/11). Endearment in Poetry
❖ Muhammad ibn Ibrahim al-Ya`muri said:
“Preserve good morals for yourself and distinguish
Through it the hidden among ugliness and beauty.
If your wealth is too little to give your companion,
Then meet him pleasantly, whenever you meet.”  Rawdat al-`Uqala’, Ibn Hibban al-Busti (p. 64).