Explanation

  • Used to describe something that is extremely difficult, slow, and frustrating to do, especially obtaining information or cooperation from someone who is unwilling or reluctant.

Origin

  • Refers to the literal act of extracting a tooth, which was historically (before modern dentistry) a painful, difficult, and unpleasant process.
  • The phrase vividly conveys the struggle and frustration involved in the task.

Alternatives

Slang/Informal:

  • A real pain in the neck/ass. (Describes something annoying/difficult)
  • A nightmare. (A very difficult or unpleasant experience)
  • Like getting blood from a stone. (Specifically for getting money or information from someone unwilling)

Vulgar/Emphatic:

  • A total fucking nightmare.
  • Hard as hell.

Milder/Standard:

  • It required considerable effort.
  • It proved remarkably difficult.
  • Obtaining cooperation was challenging.

Situational Appropriateness

  • Mostly informal to semi-formal.
  • The imagery is strong, so while acceptable in many professional contexts (especially among colleagues venting), it might be slightly too informal or graphic for very formal reports or high-level presentations. Use judgment based on audience.

Misunderstanding Warnings

  • The literal meaning is gruesome, but the metaphorical meaning of very difficult and frustrating is well-established and unlikely to be misunderstood in context.

Examples

  • Getting him to talk about his feelings is like pulling teeth.
  • Trying to get the kids to clean their room is like pulling teeth.
  • Extracting the necessary data from their outdated system was like pulling teeth.

Dialogue

Teacher A: How did the parent-teacher interview with Mr. Jones go?

Teacher B: Ugh, it was like pulling teeth. He barely said a word, and getting him to discuss his son's progress was incredibly difficult.

Teacher A: He's always like that. Very reserved.

Teacher B: Tell me about it! I felt exhausted afterwards.

Social Media Examples

  • Tweet: Trying to get a straight answer from customer service is like pulling teeth. 😩 #CustomerService #Frustrated
  • Facebook Post: Spent all morning trying to get my toddler to eat vegetables. It was like pulling teeth! Any tips from other parents? #Parenting #ToddlerLife
  • Reddit Comment: Getting my group project members to actually contribute? Like pulling teeth.

Response Patterns

  • Oh, I know that feeling!
  • That sounds incredibly frustrating.
  • Why are they being so difficult?
  • I can imagine!
  • Persistence pays off... sometimes.

Common Follow-up Questions/Actions

After someone describes something as like pulling teeth:

  • The listener often expresses sympathy or shares a similar experience.
  • They might ask why the task was so difficult or why the person was uncooperative.
  • They might ask if the person eventually succeeded.

Conversation Starter

  • No.
  • Used to describe the difficulty of a task or interaction that has already occurred or is ongoing.

Intonation

  • Strong emphasis often on pulling teeth. It was like PULLING TEETH.
  • Usually spoken with a tone of exasperation, frustration, or annoyance.

Generation Differences

  • Widely understood and used across all generations.

Regional Variations

  • Common in all major English-speaking regions.
Level playing field