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I reckon gradually and naturally while he or she isn't looking. And then after that your crush will start to like it. At least that's what i tried and it worked.

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If your shy, like me, have a friend randomly text him something like have you and (your name) ever held hands?

Of course if you havent he will say no.

Have your friend say:

Why not?

And if he says: Im not ready to or something like that

then don't, but if his repsonse is something you think would mean he wants to but is scared to have your friend give him advice.

Like, well, I've talked to her to she said she was scared to.

But really all you have to do is grab her hand, I'm sure she will enjoy it!

Next time you guys meet up if he doesnt just grab his.

Try rollerblading,

When youfall if he offers a hand to help you up take it and don't let go but if he lets go or shows a sign of i don't want to hold your hand let go.

The cellphone texting way is how i found out he wanted to hold my hand to, now just have to figure out the rest :).

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13y ago

What else can I help you with?