So here's a prompt that really felt personal.
The last goodbye was with a best friend of mine for over two years, though we only really were at our best the first few months and then slowly slowly, the closeness we found became confusion and emotions neither of us were ready for. We did stop talking many a times over the last years, but it wasn't till a few months ago we both (well me) decided it was best we say goodbye.
I've probably never felt so vulnerable and scared and sad and emotional all at once before.