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I should start this out by saying that @sarah_r92 's thread about things people always carry with them got me thinking about those things leading to conversations with other people. :) For instance, I have a keychain of Cooper, a bright pink and blue giraffe/llama-like character from the movie "Trolls" hanging from my bag, and sometimes people will comment on it, asking questions like "who is that?" or saying "I like that guy hanging on your purse - what's his name?" etc. Then I get to sort of talk with them about Trolls for a minute or two and it usually leads to a conversation that is more or less "safe" or familiar territory for me. Has anyone else experienced this? :)
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I have tried to socially engineer this very thing and failed so many times; I can not get it right. I would love some tips on how to pull off objects as conversation starters if anyone has any.

In my wilder years I got facial piercings not as a way to rebel but largely for the purpose of being conversation starters. It did not work. All it did was make middle class white women scared of me, which albeit was amusing but definitely not worth the care plus getting caught on everything - I ended up taking them out.

The best luck I ever had was with jewelry. My silver Celtic band has started a few conversations, usually people want to know the significance and origin of the pattern. Also, tangentially, my baking soda box chain pendant has drawn some curiosity from people who don't understand the significance of an iced out box of baking soda in the form of jewelry hanging from a gold chain. I usually just tell them I'm a big fan of products that contain baking soda as an active ingredient, that's just easier, leaves more open ends to build upon.
I may try to use this idea to decorate my desk at work....but so far I haven't come up with anything. I agree with @Gritches that jewelry can be a great conversation starter.
I am always with books. Sometimes it starts a conversation and then I am supremely happy!
Not really with objects (except a random man who walked past me and commented that he loved my handbag - it's a Star Wars one) but definitely with tattoos. I have a C3PO one and am forever having people start conversations when they spot it.
I've done that and in my experience NTs do it too. Yesterday I went to the drug store and the cashier said she liked my sweater. I said thanks and I put my purse on the counter and then she said she liked my purse too. My old therapist had a receptionist. Every since week, regardless of what I was wearing, she'd say I looked nice. She didn't seem like an aspie but I found that behavior odd, I guess she was just struggling for conversation or trying to promote a good body image or something. When I take art classes sometimes people say like like my art and sometimes I'll say I like their art. Objects do help me to make conversation.
One time, I bought a teddy bear at a thrift store and I was carrying it around with me on an errand to the grocery store (there was no room in my purse for it). An elderly woman approached me, grabbed the bear, hugged it, and asked "what's his name?" she informed me that she had a collection of teddy bears at home and she was happy to meet someone else who enjoyed them. That has been the most positive experience I've ever had with taking a plush with me in public.

Another time I had a less than positive experience. I had brought my plush Brionne (a Pokemon) with me to my psychiatrist's office when another patient asked me, "what kind of stuffed animal is that?" It wasn't the question that bothered me, but the tone the person used and the expression on their face. They looked really mean. I avoided eye contact and quickly rambled off some information about Pokemon and where you could buy one. That was definitely my most uncomfortable experience with bringing a plush toy with me in public.

I know, I know - I should really stop taking my plush toys with me. If I can't handle the social ramifications of doing something out of the ordinary then I should probably just stop doing it altogether... I mean, for goodness' sakes, I can't even wear my Pokemon Trainer hat without breaking into cold sweats! (I would rather die than do a full cosplay!)

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