What it means
A lollipop lady is the school crossing patrol worker, usually a woman, who gets kids and parents safely across the road outside school with that big round STOP sign on a pole. In the UK, loads of people call her the lollipop lady because the sign looks like a giant lollipop, and she’s the one freezing traffic while the school-run chaos waddles over.
Usage examples
"Nearly got clipped rushing to the gates, and the lollipop lady barked, Oi, wait. She stopped the traffic, gave me a look, and waved us across."
"Our lollipop lady at the primary school has been at her post for twenty years, the kids in Year Six still call her Mrs L and the parents bring her a card every Christmas."
"The new lollipop lady at the busy junction near the church has already stopped two SUVs from running the lights, she takes the job seriously and the local paper did a feature on her."
"The lollipop lady outside ours clocks every dodgy driver before they’ve even hit the crossing, proper road queen."
"If the lollipop lady’s not out yet, the whole pavement just sort of bunches up waiting for her to work her stop-sign magic."
Where it comes from
It’s a British nickname that took off with school crossing patrols in the mid 20th century. The round handheld STOP sign looked like a giant lollipop to kids, so lollipop lady stuck in everyday speech, even though the official job title stayed much more plain.
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