Congrats on becoming a landlord, welcome to the "party"!
If I were you, I would be firm with needing rent more timely, I would still contact the male because she can't kick him off the lease, and I would have a conversation with her along the lines of "this is clearly not what either of us signed up for, is clearly not working, and what can we do to get you to a lower cost living situation as soon as possible?" Work with her on that. It may be overwhelming to her to think about moving but you might be able to easily make some aspects of it easier depending on what feels heaviest to her. Keep your goal in mind, a paying tenant, her or the next tenant. You can also tell her that you are going to start the paper trail so that you don't get stuck with unpaid rent, but that it will be rescinded once she gets up to date on payments. Be clear that you are not messing around, have some wiggle room and grace, but that you have bills to pay too. You gave the mouse a cookie and now she is expecting you to give her the milk too. You have every right to draw the line at the cookie only. In truth you don't have a lot of power over when and if she pays, but you can and should use the power you have.
We have this clause in our agreement and we talk about it before they move in so that they are clear who the primary is and what that means.
In the event that Tenants decide they no longer want to live together, ___________ will be considered the primary Tenant to make decisions about modifying or terminating tenancy. Deposits will not be returned (full or partial) until all tenants move out.