According to one study, an awkward silence lasts approximately four seconds. If it happens regularly, enough awkward silences can utterly derail a date. Over the past few years, I’ve compiled a list of the most interesting questions I’ve ever come across that lead to engaging and flowing conversations. PartyQs has over 750 hand-curated questions in four categories: Fun, dating, deep questions and party questions.

Examples:

• If you received $10 million but could only spend it on things that start with the first letter of your first name, what would you buy?
• What’s the best typ...