60 Hard Questions To Ask When Dating In 2023

Before you wonder, let’s clear something up. No one wants to ask or be asked an awkward question—so why bother? Unfortunately, asking the awkward hard-hitting questions is how people can really get down to the nitty gritty of who they’re dating and where things are going in the relationship.

Though awkward questions are nobody’s favorite thing, here are 60 that will help clarify the situation you’re in and the personality of who you’re dating.

The Serious Questions
These questions should probably be worked in slowly, but should definitely be discussed eventually. If you’re passionate about having kids one day or throwing a huge wedding, it’s better to find out if the person you’re dating is on the same page. Some subjects are negotiable, but for many, the following awkward questions are potential deal breakers.

  1. Do you want to get married one day?
  2. Do you anticipate having a big wedding or small wedding?
  3. Is it important for you to have a traditional wedding or would you be open to something like eloping?
  4. Do you want to have kids one day?
  5. How many kids do you want to have?
  6. Where do you want to live?
  7. Are you interested in buying a house?
  8. How important is religion to you?
  9. What kind of debt are you in?
  10. Are you happy in your career?

People are always told to avoid talking about their exes, but that’s only true to a certain extent. As things start to get more serious between you and the person you’re dating, it can be helpful to learn more about how your partner views their past dating experiences.

  1. Have you ever been in love with anyone?
  2. Have you ever lived with someone before?
  3. How long did your longest relationship last?
  4. Why did your last relationship end?
  5. What matters to you most in a relationship?
  6. Do you see us together in five years?
  7. What are your goals for dating?
  8. Do you love me?
  9. Have you been married before?
  10. Do you think about marrying me?

The Physical
It’s really important to maintain an open dialogue when it comes to sex and your sexual health. (Both of your sexual health!) Some of these questions will naturally come up as you two get to know each other, but it’s important to check back in from time to time to ensure you’re both happy, healthy, and comfortable with one another.

  1. What kind of birth control do you take/prefer?
  2. How often do you get tested?
  3. Have you ever had a sexually transmitted infection or disease?
  4. How would you feel if you and I accidentally got pregnant?
  5. What makes you feel comfortable in the bedroom?
  6. Do you feel like you can talk to me about sex?
  7. How old were you when you first had sex?
  8. Is there anything our physical relationship is lacking?
  9. What can I do to make you feel desired?
  10. Do you watch pornography?

About the Author

A prolific love author who specializes in creating love stories often focused on the romantic connections between people which readers can identify with.