Wirecutter’s Jason Chen Breaks Down Your Biggest Black Friday & Holiday Shopping Doubts

Jason Chen answers your top Black Friday shopping questions. Jason Chen answers your top Black Friday shopping questions.

3. The Biggest Black Friday Doubt: “When Should I Actually Buy?”

The main Black Friday question: the best time to make a purchase.
The main Black Friday question: the best time to make a purchase.

This is the most common question Jason Chen receives.

His answer:
“Buy when the price hits its historical lowest point — not based on the date on the calendar.”

Jason Chen’s buying timeline strategy:

  • Early November → Best for laptops, tablets, headphones
  • Mid-November → Best for early gift items, kitchen appliances
  • Black Friday week → Peak discounts on TVs, smart home devices
  • Cyber Monday → Best for software, subscriptions, online-only items
  • Early December → Toys and gift sets rebound in price
  • Mid-December → Prices rise due to shipping pressure

Shoppers often assume that waiting for the actual day of Black Friday will yield the steepest discounts.
Chen stresses that this is outdated thinking.