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What it means

Means keeping your options open and not fully backing one side, so you're covered whichever way it goes. It often has a mildly teasing edge, used for someone who's playing safe, sitting on the fence, or trying to stay mates with both camps till the dust settles.

Usage examples

"He’s telling HR he’s staying, but he’s still interviewing elsewhere. Proper a bob each way, just in case the promotion falls through."
"He never says yes or no, always a bob each way."
"We put a bob each way and backed both contractors, just in case."
"Don't ask Dan to pick a side yet, he's gone a bob each way till he sees who's actually paying for the drinks."
"She praised the old manager in the meeting, then backed the new one in the pub. Bit a bob each way, that."
Tone
Ironic Funny
Where it is said

Where it comes from

It comes from British betting talk. An each-way bet puts money on a horse to win and also to place, so you've got a bit of cover if it doesn't come first. A bob was old slang for a shilling, so putting a bob each way became a neat way to mean hedging your bets in everyday life.

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