in: Dating & Relationships

Outside-the-Box Questions to Take on Any Date

First, second, third, or twelfth! It’s time to feel confident about conversation no matter what. We’ve got excellent stand-by questions to take on any date.

Dates can be hard when you want to balance between being your authentic self and feeling engaged in confident in how things flow.

Coming up with original topics for conversations on dates without resorting to “how ’bout this weather?” can be challenging, especially when you’ve been on so many different dates. We can start sounding like a broken record asking the same questions and talking about the same topics.

When you become a great at conversations and charismatic, you have the ability to bring out the authentic side of people. When you do you that, you can figure out what your true compatibility is really all about.

These tips will show you the how and what of the best types of questions to ask for interesting, authentic conversations—a sure fire way to build intimacy on your date.

How to Be a Great Date Conversationalist

Being a great conversationalist on a date is counterintuitive. Most try by coming up with a list of funny stories to tell, witty comments to shoot off, and try to impress the other person with their commentary. We are so focused on ourselves and trying to show our dates our feats of accomplishment we forget that taking an interest in them increases our likelihood of a second date (if we want one, that is).

Becoming a good conversationalist begins with showing an interest in the other person while having a positive mindset.

A concept theorized by Elaine Hatfield on emotional contagion says we can literally catch another person’s mood. So if you are enthusiastic about them, they will be enthusiastic about you. When you show interest in someone else, they in turn will become more interested in you.

This is the reciprocity of energies.

A charismatic person focuses their attention on you and remains in the present with the conversation. They balance between asking questions and talking, showing a genuine interest in learning who you are. They also steer the conversation to find subjects that excite you and make you feel good about yourself.

All these things help to boost their likability factor and it’s all something you can incorporate on your dates as well.

Remember that how you feel about your date is reflected in your own body language. You have the ability to impact the other person’s enthusiasm on the date simply by changing your own energies.

What makes for an interesting conversation?

When you Google “first date conversations” you will find the search will bring up hard fast rules about what NOT to talk about.

  • Avoid anything related to your ex or previous relationships.
  • Avoid politics and any work-related conversations.

The problem with these rules is people can come across as boring for the sake of being politically correct and polite during the date. We hide our real opinions and our individualism. To create exciting date conversations means taking the risk to ask outside-the-box questions and to have those non-traditional, polite dialogues everyone has when they meet someone new.

People want to feel alive and invigorated. When they experience these feelings you will become more memorable and they will want to go out with you again. You can evoke these feelings out by asking interesting questions to make your dates more enjoyable. Below are some guidelines.

Choose Controversial Topics

A study conducted by Dan Ariely1 found that people tend to gravitate toward topics that are easy to talk about but no one finds enjoyable. Subjects such as “What do you do outside of work?” or “How many siblings you have?” are boring, mundane, safe topics.

Instead, choose questions that are interesting and personally revealing. These questions include:

  • How do you feel about the current Presidential candidates?
  • In what way would you like to be famous?
  • If you could change anything about the way you were raised, what would it be?
Share Secrets

In a book called Click, the authors studied the psychological interactions that make us bond together with certain people over others. They identified the key points that accelerated connections in our work and relationships, making it great for its application in dating.

Examples of revealing questions include:

  • Given the choice, who would you like for a dinner guest and why?
  • Before making a telephone call do you rehearse what you say and why?
Talk Travel Over Favorite Movies

Richard Wisemen conducted a study in his book Quirkology that showed when first date conversations revolved around movies or films only about 9 percent of couples wanted to see each other again versus 18 percent if the conversations were about travel. They found men and women have a wide range of interests in movie genres. For example, 29 percent of women like musicals versus 4 percent of men. This difference does not create similarities and agreement during conversations.

The reason travel is a great conversation topic is it evokes positive feelings in each person, so they appear more attractive to one another. Remember emotional contagion? Talking about travel helps people dream and plan wonderful holidays. If they are with you during this discussion, they will associate these positive feelings with you.

Remember to keep an open mind during conversations and consider other points of views because controversial topics are often personal and revealing.




About the Author:

Candace Wong

Are you using technology to find love? Feel like you are running out of men to date and frustrated by the non-committals but ready for a real relationship? My name is Candace, a love coach for single, professional women looking for real, long-lasting love. If you are ready for commitment, learn how to identify men who are ready too with my free online e-guide at


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