60 Awkward Questions to Ask the Person You’re Dating

A woman who's asking her boyfriend awkward questions covering her face and laughing behind her fingers.

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?

The Past, Present, and Future
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 healths!) 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?

Family History
Discussing familial history can be really tough for people, especially if they come from an unconventional family, or one that has experienced grief or suffering. It’s important to learn all that you can about someone’s family history to better support and understand them as a partner. When appropriate, consider asking them the following questions.

  1. Are you close to your mother?
  2. Are you close to your father?
  3. Do you have living grandparents?
  4. Do you have siblings? Are you close to them?
  5. What traditions from growing up are you keen on keeping up?
  6. Is there any part of your childhood you’d like to leave behind?
  7. Where did you grow up as a child?
  8. Do you consider your parents’ relationship to be a healthy one?
  9. Was anyone in your family an addict?
  10. How can I support you in your grief/processing with your familial relationships?

Vices
This is certainly not a first date conversation, but eventually, as things get more serious, it may be worth asking the following questions to learn more about your partner. You will also get to learn more about how you can support your partner through anything they may struggle with in the future.

  1. What is your biggest vice?
  2. Do you consider yourself addicted to anything?
  3. Do you drink alcohol?
  4. Do you smoke cigarettes?
  5. Do you do drugs?
  6. Have you ever done drugs?
  7. Have you ever had a DUI?
  8. How old were you when you had your first drink?
  9. Do you vape?
  10. What drugs would you consider doing? 

Beliefs
From religion to daily routine, the word “belief” can be a major one. When dating someone new, or even after dating someone for a long time, it’s important to figure out where you two land on some of the more important day-to-day aspects of life. Figuring out your partner’s priorities, interests, and values is key, even though it can be a tough conversation.

  1. Do you believe in God?
  2. Did you grow up going to church?
  3. Do you consider yourself a faithful person?
  4. How familiar are you with the Bible?
  5. Would you raise your children in the church?
  6. Do you identify with a political party?
  7. Do you feel comfortable telling me who you voted for in the last election?
  8. Do you follow local/national news?
  9. Do you believe in [pick the topic you are most passionate about]?
  10. Are you registered to vote?

There are so many different ways to ask the above questions. Make them your own and really make sure you’re in a comfortable and appropriate setting to fire some of these off. Don’t ask someone out on a first date and bring this list along. Work them into your regular conversations while getting to know each other in a lighter, more fun way. Before you two decide to thoroughly commit to one another, make sure some of the bigger value-based questions have been discussed. They can be awkward, but they’re also extremely important. A healthy relationship is one that can discuss the tough stuff. So don’t be afraid to get a little awkward. 

Jessica Tholmer

Freelance Writer

Jess Tholmer has been writing on the internet for what feels like most of her life. After studying English Literature in school, she has leaned into her degree and is a full-time content writer, social media manager, and freelance contributor to websites like HelloGiggles.com. You can find her @tholmz on Twitter and Instagram!

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