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Winter Date Ideas That Make Conversation Easy

Cold weather is good for dates: hot drinks, lights, skating and nobody looking cool. Here are eight winter date ideas, and why each one makes talking easy.

Winter dates have a secret advantage: nobody looks cool in a hat, on skates or holding a mug with both hands. When you’re both a little ridiculous, it’s easier to relax. Here are eight ideas that do half the work for you.

Ice skating

Most people are bad at it, which is the point. Holding the wall together and laughing about it beats any opening line.

A holiday market

Lights, cinnamon and stalls full of things to judge. Find the strangest ornament on sale and ask for their verdict.

A walk to see the lights

Side by side, warm drinks, something pretty to look at. It’s easy to make it longer or shorter depending on how it’s going.

A day on the slopes

Even if one of you sticks to the beginner slope, the chairlift is ten quiet minutes side by side with a view. Save a full day for a later date.

A late movie at a small movie theater

Pick something old or strange, then go somewhere warm to argue about the ending. The talk afterwards is the real date.

A board game café

A game gives your hands something to do and gives you plenty to tease each other about. Choose one you can learn in five minutes.

Cooking something warm

Soup, fondue or anything that bubbles. Good for a second or third date, when a quieter evening feels right.

Sledding

Childish in the best way. Bring something hot to drink and don’t take the first run too seriously.

Keep the first one short

Cold weather is a good excuse for a short first date: an hour of skating, then a hot drink. If it goes well, the next plan almost makes itself: “Same time next week, somewhere with heating?”

Lines to borrow

  • Suggesting skating: “Want to go skating on Friday? I’ll be the one clinging to the wall.”
  • At the holiday market: “We have to find the ugliest ornament here. Winner gets a hot chocolate.”
  • On the chairlift: “Ten minutes up here and no phone signal. Tell me something I don’t know about you.”
  • After a late movie: “Okay, I need to know what you thought of that ending. Hot drink?”
  • Ending a short date: “That was the best kind of cold. Can I take you somewhere warm next time?”

Practice it

The Holiday Market is free to play every December: a line for hot cider and a very ugly glass pickle. The Ice Rink unlocks at Regular and The Chairlift at Charmer, both free with an account.

Practice it

The Ice Rink

Try what you just read on a character who is not real. It takes about two minutes. Free, no account needed.

Play The Ice Rink

More scenes for this: The Holiday Market, The Chairlift.

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