What it means
Means something's painfully hard work to get out of someone or get done at all. You use it when every answer, detail, or bit of progress has to be dragged out inch by inch because the other person's being stubborn, silent, awkward, or just giving you absolutely nothing.
Usage examples
"Getting Dave to admit he nicked the last Jaffa Cake was like pulling teeth. I asked three times and got nothing but shrugs."
"Getting the teenager to say how school went is like pulling teeth, all grunts and shrugs."
"Trying to get a straight answer out of him about where the money went was like pulling teeth."
"Getting the kids into the car this morning was like pulling teeth. Nobody could find their shoes and everyone was sulking."
"Getting any useful feedback from that client was like pulling teeth. Every email back was two words and a typo."
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Where it comes from
This one goes back a long way in English and grew out of the very literal misery of tooth-pulling, especially back when dentistry was rough stuff and nobody fancied being in that chair. The image stuck because it instantly screams pain, resistance, and a job that takes way too much out of you.
Other ways to say it
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