What If Wednesday

For imagination, insight & chemistry

Sometimes the easiest way to learn about someone is to step outside of reality.

The What If Wednesday deck is a curated set of 48 hypothetical, scenario-based questions designed to spark curiosity, reveal values, and create effortless connection. By exploring imagined situations, these questions invite honest answers without pressure — making depth feel playful, not intrusive.

From light, imaginative scenarios to thought-provoking “what would you do if” moments, this deck helps you understand how someone thinks, feels, and chooses — without asking anything too personal, too soon

This deck is for:

• Playful first dates that still feel meaningful

• Learning someone’s values through imagination

• Conversations that flow without awkward pauses

No right answers. No expectations. Just curiosity, creativity, and connection.