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I'm travelling through Japan and I've been asking cool people I meet to sign my shirt in Japanese. I've been saying this:

sain shitemoratte ii desu ka?

And they always ask sain? and laugh then realise I mean my shirt.

Is the shitemoratte bit accompanied with me pointing to the shirt?

Or can I just point to my shirt and say sain ii desu ka?

How would I say "I am travelling Japan asking cool people to sign my shirt, is it okay if you sign it too?"

Thank you in advance! Apologies for the potentially wrong formatting.. I come from SO

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I'm not sure how much you have learned about Japanese grammar but I think it would be helpful to breakdown your phrasing a bit just so you know what you're saying. The "sain" is a loan word from English and it's what they use when signing a document. The "shitemoratte" means someone doing something for you. The "ii desu ka" means "is it alright?"

There are many ways to ask someone to do something for you in Japanese but if you don't feel like memorizing many phrases what you have works just fine. You just don't have an object in your sentence so people probably don't know that you're referring to the shirt. You could say:

Kono shyatsu ni sain shitemoratte ii desu ka.

Could you sign this shirt for me?

As for the phrase you wanted to say, you could say:

日本で旅しながら、色んな人にこのTシャツにサインしてくれるようにお願いしています。サインしてもらっていいですか?
(Nihon de tabi shinagara ironna hito ni kono shatsu ni sain shite kureru you ni onegai shiteimasu. Sain shite moratte ii desu ka?)

As I'm traveling Japan, I'm asking people to sign this shirt. Will you sign it, too?

It's a little long, but it gets the message across.

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If they're confused, you maybe could be more specific:

僕のティーシャツにサインしてもらってもいいですか?(Boku no tiishatsu ni sain shite moratte mo ii desu ka?) Could you sign my shirt?

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