Contacts linked within contacts, and reportability

Happy Holidays, all! I have an odd question that I am hoping someone is able to assist with. As of now we have assistants linked to whomever they assist. For example, if Jane is an assistant to John, we have a custom field, using the lookup relationship field type, within our contact page which allows a user to pull up John's profile and have the ability to click over to Jane's profile; both Jane and John have their own record IDs. My goal is to be able to pull a report that extracts email addresses for both Jane and John based on criteria only found in John's profile. So far I have been able to pull a linked report which shows Jane is associated with John, but I haven't been able to find a way to include Jane's specific information in the linked report. Is it possible to pull this kind of report, or should I just manually add each assistant to whomever they assist using a non-linked field?

Apologies for the confusing question, and thanks for any help you're able to provide!

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