If your trip group chat goes quiet at the word “budget,” try asking everyone to pick a side. Start with a few would-you-rathers about where to go, then try the planning questions.

Start with this one and make everybody answer before anyone explains:

Count the hands. Then go around and ask why.

Every question here comes from Lolo Cards - 5,200+ conversation cards for iPhone.

Pick a side: beach, mountains, city

If you’re stuck on where to go, try these as a game. Nobody is booking anything yet.

For this round, no “it depends.” If someone says it, ask them to pick the answer they would give if the whole trip depended on it.

Give anyone who’s unsure time to answer. Then ask a follow-up: “What would make it a yes for you?”

Plan it or wing it

If some friends want a plan and others want to wander, try a round about planning styles before you leave.

The last two are “who” questions, so everyone points at the same time. Let whoever gets pointed at respond.

Once the pointing is done, try making a deal. The planner picks the first night and the first morning. The wanderer gets one open afternoon with no schedule. Check that the arrangement works for everyone.

Illustration: a penguin with a neat itinerary and a penguin with a beach ball pointing in opposite directions on a sunny pier
Planner and wanderer, same trip

Researchers studying pairs of friends traveling together found that friendships grounded in goodwill were more likely to use compromise and work toward a solution together when handling disagreements (Journal of Travel Research, 2024, listed in Sources). That finding concerns pairs of friends. A game won’t create goodwill, though it gives your group a place to practice saying what each person wants.

Travel trade-offs

Now make it harder. Ask everyone what they’d be willing to give up.

For the food-versus-weather question, let each side make a one-sentence case, then vote again. See if anyone changes their mind.

Use the teleport question to ask what people enjoy or dislike about the journey itself, especially if you’re planning to share a rental car.

When you’re stuck at the gate

If your flight is late and the group is slumped over the carry-ons, try a short round.

For the first one, each person describes their 24 hours in one breath, and the group votes on whose plan they would actually join. For the second, go around and name the thing you forget.

Keep it short at the gate. Three or four questions, then stop. If the boarding call comes mid-answer, finish it on the plane.

Illustration: two penguins sitting on suitcases at an airport gate, passing a question card between them while a plane waits outside
A delayed flight is a good time for one more card

How to run the round

Try these rules with a group of three or more:

  1. Answer first, and keep it short. The host picks a side in one sentence and does not defend it. That shows everyone how short an answer can be.
  2. Vote at the same moment. Count to three and raise a hand or point so everyone chooses before seeing the other answers.
  3. Ask why only after the vote. Give everyone a turn to explain.
  4. Skip what flops. Say “next” and move on.
  5. Write down the results. If the beach wins by four hands to one, use that as a starting point for planning. Check what the mountain voter needs before booking.

New to the format? How to play would you rather covers the basics. If the trip is also an excuse for a party, there are more openers in fun questions to ask at a party. Find more dilemmas, from silly to hard, in the would you rather questions collection.

A study of people who found travel partners online suggests that being a good travel partner involves more than shared interests. In the CORDIS summary, one of its authors advises people traveling with family to set goals and expectations before packing. That study was about strangers who met online, so its findings may not apply to your friend group. Use the round to start talking about expectations, then discuss what everyone needs from the actual trip.

Sources