Woocommerce - Add additional item if some item wants to be added to the cart?

Is there a way for me to force the user to select one from a variety of products into the cart when they try to add a specific item to the cart?

So lets say I have a Product like a blank USB and the customer chooses what product/software they would like loaded on the USB. I don't want to turn this in to a variable product as there could be hundreds of option. I don't want a customer to just add this item to the cart and purchase a blank USB. I want the customer to be asked What they would like to be loaded on the USB before purchasing. Basically buying the USB and the software together.

I was looking into this thread: https://stackoverflow.com/questions/52655141/woocommerce-if-specific-product-is-in-cart-disable-specific-checkout-fields-that and I can approach this buy preventing the customer from going through the checkout process if this item is in the cart. However I would like to think there's a better option for me like if they added the USB to the cart, there is a popup or the customer gets directed to another page that loads in options for the customer to choose from to add to the cart.