Everyone has their list of, “first date,” questions. However, I’m a firm believer that the best questions are the ones you ask, before the date. Why? How often do you hear about, “terrible dates, wasted time, and money?” Why would you wait until you’re out on a date, to figure out if someone wants kids? Some of us don’t ask that question until later in the process. Seriously. Most of these dates would be prevented, had the important questions been asked before the date. Are these questions foolproof? No.

Break The Cycle

At some point, we have to stop repeating the same process over and over.  One or two conversations barely touching the surface, and boom, you’re on a date. Now the romantic feelings have set-in, the infatuation has taken over, and the illogical outcome is inevitable.  You’re not thinking properly, the smiles and good-looks have you overwhelmed like a house full of unruly kids.


you’re sitting on the date wondering how in the world you arrived at this destination. Your dating GPS would’ve rerouted you, but instead, you ignored it. Now, you are on a date with someone who is completely incompatible with you. You’re not on the same page, are you? Maybe they misrepresented themselves. “Catfish,” for dinner anyone? “No thanks, I’ll pass,” is what you’re thinking. All because you jumped the gun.  I’ll say it again…

“At some point we have to stop repeating the same process over and over.”

About The Questions

Photo Credit: Jonathan Simcoe

Below I will outline these questions by priority. Use your discretion you when you ask. Remember, these questions are only guidelines for your, “pre-dating,” experience. You don’t have to ask them all. At the end of the day, you will still need to place yourselves in front of each other, and talk face-to-face.  Now it’s time to decide whether you are parallel, or symmetrical.  Or, do you complement each other? Don’t know the difference?

“Complementary and symmetrical relationships have potential for both positive and negative attributes. Parallel relationships are generally considered to be the most preferable type because it is a blend of the desirable qualities of the other two.” Read more here.

That being said, you will need to discern between honesty and deceit.  Incompatibility and commonality. By the way, these questions can be prioritized in any order you choose.

Remember, everyone you meet isn’t meant to be your significant other. Some people you date will become long-time friends, or business partners.  Or, they will simply, fade-to-black. No matter what they become, make sure you choose wisely.


High Priority Questions

  • Do you have any children? If so, do you want to have any more children?
  • Do you believe in a higher being? If so, what do you believe?
  • What is your dating style? Multiple people, or get to know one person?
  • How do you feel about marriage? What is your plan to get there?
  • (if they have kids) What is your relationship like with the other parent?
  • Do you prefer to text, email, phone, or in-person?
  • Is there anyone out there that might feel like you are in a relationship with them?
  • What are your hobbies or interests?
  • Do you smoke or drink?
  • Do you have a criminal record? If so, what were the crime(s)?
  • When was the last time you were tested for STDs? Would you take an STD test prior to us potentially having sex?

Medium Priority

  • In regards to dating, what type of man/woman are you? Traditional, Modern, or a little of both?
  • Were both of your parents present when you were a child?
  • What was your relationship like with them growing up? What is it like now?
  • Where do you see yourself in the next 5-10 years?
  • Do you believe in courtship? If so, what does that look like to you?
  • When was the last time you had sex?
  • When was your last relationship, and why did it end? What role did you play in its demise?
  • When it comes to marriage, do you believe in an equal partnership or the man is the head of the household?

Low Priority

  • How does happiness look to you in a relationship?
  • When there’s a disagreement, how do you resolve conflict?
  • How often do prefer your mate to communicate with you?
  • Do you live alone? If not, what does your living situation look like?
  • Do you believe in co-habitation

Basic Priority

  • What are you most passionate about?
  • Do you like adventures such as nature hikes, cycling, skydiving, or white-water rafting?
  • Are you a home-body, or socialite?
  • Do you like to cook? What’s your best dish?
  • Did you vote for Trump? (kidding, but not kidding)

Optional Questions

  • Where are you from originally? What was it like growing up here/there?
  • Do you believe in taking on your husband’s last name?
  • What number will your husband fall on the priority list?

Questions That Can Be Asked At Any Point

  • What is your sexual orientation?
  • Have you ever been with someone of the same-sex?
  • Where you born a male/female?
  • How do you feel about cohabitation before marriage? Do you feel like it’s necessary?