I worked at Progressive for 19 yrs.

No, that's not normal.

Either go through them. Ideal.

Go through your insurance and let them subro. Keep in mind getting your deductible back isn't a guarantee.

No.

That is completely manipulative and too late.

If you're willing to work through the issues, then why dump her? You should've communicated and tried to fix them.

You dumped her. Stop trying to make her feel like there's a chance down the line.

If you weren't mature enough to work through the issues, then you're not now.

It smells of insecurity on your end. Like you're regretting breaking up.