'Accept my sincere condolences on the loss of..'.Are you good at conveying this?

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Every other day some body is dying in every corners of the world.We can't help it but to feel sorry for them.Today my boss' mom passed away I was real awkward at my way of 'Condoloncing'. A letter of condolence well-written can help ease the sorrow for a grieving person coping with the death of a loved one. But not every one is good at it if i am not wrong.I am bad at it. A condolence letter acts as a writer's sympathy and compassion to the grieving person.It also reminds the grieving person that they have friends and/or family who are with them during the difficult times. Ironically,i haven't written a single such letter in my life.And i am bad at giving condolences in person as well.The only sentence i could manage is 'I am sorry,dear/fan/whoever'. You tell me how good are you with it? I know girls(especially) are really gifted with giving condolences.But guys??