Hi, @jbshopdev.
Greetings. Thanks for posting your question to the forums!
Discounts can definitely be tricky sometimes. While this specific discount request would not be able to be done via Shopify natively. You can absolutely try out the app Discount Ninja. While I can't guarantee this app will work, it is the most robust option in the app store. I recommend installing the app for their offered 14 day trial to see if it meets your needs. If not, I do have another option you can try.
Another option, you could acheive what you are looking for from the customer perspective. Instead of listing your products as separate listings, you can list all of the products as variants inside one single product for the sake of the discount.
Essentially, you will create a 2 for $20 product, and within that product create two variants; selection 1, and selection 2. Within each variant you will add all the qualifying products as options. Finally, you will price the product for $20. This will require the customer to make two selections to add the promotion/product to their cart. Additionally, you can maintain separate product listings of each of the products should a customer want to purchase them separately.
The only downside to this is the inventory tracking won't be automatic and would need to be adjusted manually to the parent product listings.
If inventory management is important to you, your last option is to use a bundling app instead of a discount app. The Bundlr app allows you to create product bundles for set prices while keeping inventory tracking automatic as it will connect your current product listings to bundles you create within the app.
I hope that helps! In the meantime, I would love if you can provide your domain so I can take a look at your store and see what additional support I can provide!
Skye | Social Care @ Shopify
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