5 Ingenious Types Of Questions To Ask So You'll Never Get Stuck In An Awkward Silence Again

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5 Ingenious Types Of Questions

Ah, the dreaded awkward silence.

How long is an awkward silence?

According to one study, an awkward silence lasts approximately four seconds.

Dating person #1: Hi

Dating person #2: Hi! Nice to see you.

#1: I like your shirt. You know what? I think my mother has the same one.

#2: Umm *frowns* thank you?

After four seconds of awkward silence, an infinitesimal prick of anxiety sets in. And it looms. If another awkward silence happens again, the discomfort may intensify. If it happens regularly, enough awkward silences can utterly derail a date.

Once when I was on a date, I made a comment about having kids that led to such an awkward silence that my date stood up, excused herself, and walked away. I will spare you from what I actually said.

I don’t want this to happen to you. As a result, 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 and put them in a sleek and fun app called Party Qs.

But how does an app help one have a natural conversation, you might ask? Valid question.

Party Qs is a game to play to get to know each other better. You ask the question, chat about each other’s answers, and forget about the phone. When you’re ready for the next question, return to the app and swipe on.

RELATED: 21 Great Questions To Ask A First Date (To Really Get A Feel For Who They Are)

As you are probably aware, it’s never a good idea to do the same thing on every date — creativity is the key to wooing someone to whom you’re attracted — but asking a thoughtful question at the right time can go a long way to win someone’s heart. So try using Party Qs to mix it up and keep the conversation lively with the best questions to ask your date.

1. Fun — get the laughs rolling with light-hearted and imaginative situational questions.


  • 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 type of cheese?
  • What’s the most extreme item on your bucket list?
  • What is the key to making the perfect pizza?

2. Date Night — discover something new about your partner, whether it’s date #1 or #1,254,323.

(This is the most popular category).


  • What makes you feel most alive?
  • What is something you learned from your dad?
  • Would you rather have free passes for life to all amusement parks or to all concerts?
  • What always makes you laugh out loud?

3. Deep questions — warning, these topics deal with big ideas and immersive thoughts.

Prepare for a long, interesting conversation.


  • Would you rather be famous when you are alive and forgotten when you die or unknown when you are alive but famous after you die?
  • What are signs that someone is secretly unhappy?
  • Can art be objectively good or bad?
  • Which is more important for humanity: the arts or the sciences?

RELATED: 50 Questions To Ask Your Boyfriend Or Girlfriend (Before Your Relationship Gets Too Serious)

4. Party questions— break the ice with class. Perfect for group dates, double dates, and dinner parties.


  • Would you rather travel for five years in an RV or travel for five years in a sailboat?
  • When and where do you get your best ideas?
  • Would you rather increase your reading or your exercise?
  • Are you more firm than gentle, or more gentle than firm?
  • What makes you really nerd out?

5. Random — mix it up, get creative, and swipe through a smorgasbord of all the categories.

With the substantial number of questions in Party Qs, you rarely see the same question twice (unless you favorite it with a ⭐️ ).

Keep an eye out! More categories are coming soon (e.g., Celebrity Would Your Rather, Love Languages, Word of the Day, and others). Soon, Party Qs is going to be the largest questions app ever.

I’m not trying to sell you anything (Party Qs is 100% free); I just want to get the word out and empower singles, daters, partners, married couples — anyone interested in connecting with people on a deeper level — to overcome awkward silences, have really good conversations, and be confident on their dates. It’s something I’m passionate about and proud of so I wanted to share it with you.

RELATED: 20 Intimate Questions To Ask A Guy To Really Get To Know Him

Dave Schools is the author of Runaway Millionaire and a columnist at Inc.com. He's the CEO of Party Qs, Inc.

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This article was originally published at Medium. Reprinted with permission from the author.