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Best Conversation Starters with the Elderly

I was recently at my grandmother’s ninetieth birthday. Despite the fact that it was very nice to celebrate such a wonderful milestone in her life, I was reminded of how brutal it can be trying to converse with the elderly. As I tried to be a trophy-grandson to my grandmother’s remaining friends, I realized that there is only a handful of palatable conversations to be had with the elderly. Here are a few I am going to keep in the holster from now on when I have to interact with anyone who was alive during World War Two.

“How about this weather?”

Probably the first one we all go to in any situation like this. It might seem a little basic, but sometimes the low hanging fruit is just as good as the rest of the crop. Yes, it is incredibly boring to talk about, but there is always something to be said. Either observe how the weather has been recently, talk about how you want it to be in the future, or just make up a forecast. That’s what the pros do anyway, so who’s to hate on you for telling Barbara that she should expect sun over the next week. This conversation banks on the fact that the old lady you are talking to is happy to simply have your attention. In other words, it works every time. 

“Have any of your friends passed away recently?”

This may be uncomfortable to some people, but I think it’s important to stay genuine when you talk to people. At the age they are at, odds are they will answer yes to this question. This will likely be sad, unless they’re one of those hilarious old people who have gotten really cynical about everything. These people talk about the death of their friends as casually as I recap an NFL Sunday with my friends. The only alternative to hearing about someone’s dead friends is they answer no to this question, which of course is also a good outcome.  

“What’s your body count.”

Old people are horny too. They probably don’t have enough people to talk about sex to in their everyday life, so this will probably make you and whoever you’re talking to become close instantly. Also, someone who has made ninety trips around the sun has potentially had a ton of sex. I have made it a personal goal of mine to start polling every old person I meet so I can find the highest possible answer. So far, the record I have is Gladys, with 113.

“So, what drugs did you do in your youth?”

I’m not sure if you’ve seen The Wolf of Wall Street, but it’s basically a two-and-a-half-hour ad for quaaludes. I’m by no means a hard drug guy, but man do quaaludes look fun in this movie. They have since been outlawed, and are supposedly impossible to find. I’d like to know about other drugs that have been outlawed and what crazy things were done while people were experimenting with them. These people lived through the illegalization of the white powder you can surely find traces of in any fraternity bathroom. Also, you can’t tell me a person gets to their eighth decade on this planet without picking up a fun story. Asking about the history of their drug use is a great way to steer the conversation toward these fun stories. 

“If you had to cut one of your grandkids out of your will, who would it be, and why Jeremy?”

This one is my personal favorite. This is kind of like throwing a hand grenade of entertainment into the middle of the party. Replace Jeremy with the grandkid of your choosing, and strongly suggest a reason that they might not deserve their payday. They can either agree with your reasoning, or they can give you an alternative. Odds are you’ve already tricked them into complaining about the most ungrateful grandkid of theirs, and hearing them yap about that should get really interesting really fast. You can also use their answer as a conversation starter for everyone else in the room. It will create drama fast.

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Written by TFM

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