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Adding a form

How do I add a form with questions for people to fill out when they check out?

For example- needing information about what specific course they want based on the age of their child. 

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You might want to look at a variety of integrations. Like Cognito to Square integration. Then they fill out a Cognito form and the payments in that form link though to Square.
https://squareup.com/help/us/en/article/6207-cognito-forms-and-square

We've done it with Cognito and Wufoo where we take very complex event registrations through the online forms (can gather ages, addresses, have a list of options of events to chose from - like for us it's type of housing but for you might be type of classes), and the last screen is the payment integration with Square.
It's a bit back to front from your concept that you put. You aren't starting with Square and adding a form. You're starting with the Form and adding the Square payment integration to it.

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