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I want him to like me and I want to be interesting and keep him happy. I don't want to bore him to death.

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Notice if he has trouble hearing you. Face him when you speak. Notice if he is reading your lips. Allow him to speak without interrupting him. Notice how much of the time you speak vs how much he speaks. Stay away from controversial subjects. Notice if some subjects make him sad. If he brings them up perhaps he needs to talk about “it” whatever it is However be careful not to repeatedly talk about things that make him sad. Many elders enjoy jokes. Occasionally I read the posts on this forum to my aunt (92 vascular dementia) and she enjoys answering the questions as well as hearing others replies. But be careful not to be on your phone too often as it’s isolating. Also I find elders enjoy someone watching sitcoms with them. They enjoy laughing along with someone else.
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I have found that many seniors enjoy talking about the way they used to do things. It's fascinating to hear about how people managed long ago with so few modern conveniences. They also seem to love talking about their families, pets, schools and accomplishments. Being a good listener and nice usually causes people to be drawn to you.
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People love to talk about themselves. At 88 y/o, I'm sure he has seen and done a lot. Ask about his life, family, military background and career. I love to ask for stories about growing up and relationships, where they met their spouse and how life was when they were young adults. Have fun building a new relationship!
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