How do I ask out the shy guy?

Anonymous
i found this cute boy my age in school, and we have mutual friends so we see each other every lunchtime. my friend has way more confidence than me, so she'll go up and talk to him (he's on his own quite a lot) and i'll tag along. he is so sweet and nice, but he's so quiet that i can't make conversation with him for that long that's not awkward. i want to ask him out but i have no idea how to and i like him a lot.
when i talk to him he gives good eye contact and soft smiles and sometimes i think he could actually like me, but i just don't understand him. can anyone give any tips on how to talk to him in a non-awkward convo and how to ask him out?
How do I ask out the shy guy?
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