Current phone: Never, because it doesn’t have one.
Last phone: Also never, because I had decent Bluetooth headphones.
Phone before that: All the time, but broke several sets of earbuds from snagging on things and getting frayed.
Genuinely can’t be arsed to wear a piece of wire down my clothes like I’m a small child with some fucking mittens on a string. Could not give two fucks about the 3.5mm jack dying out.