What it means
Cushioning is keeping a few romantic backups on the side while you're with someone, so there's a soft landing if the main relationship falls apart. You stay just flirty enough with the cushions to keep them warm, without fully committing to anyone. It's hedging your bets in dating, and pretty unfair on everyone involved.
Usage examples
"Turns out he was cushioning the whole relationship, texting two other people just in case."
"A bit of harmless flirting or full-on cushioning? There's a line and she crossed it."
"He wasn't confused, he was cushioning. Man had a whole emergency contact list for his love life."
"If you're still DMing your little backup flirts while calling someone your person, that's cushioning and it's grim."
Where it comes from
The term comes from the literal idea of a cushion being something soft you fall back on. It showed up in online dating and relationship talk in the 2010s for keeping extra romantic options hovering nearby, so if your main thing crashes, your ego and love life don't hit the floor full force.