The Fundamentals: Things to ask at the start of a relationship

This is a concise summary of lists I've found on the internet as well as the very good book "101 Questions To Ask Before You Get Engaged".

Except those questions are the kind of questions to ask at the start, not years down the line. Potential incompatibilities must be rooted out as early as possible.

Those are not "questions to get to know each other", you can find that elsewhere on the internet. These are all things that could be dealbreakers or hard compromises, and are, at the very least, things you and your partner must know about each other before deciding to commit to a relationship.

For the tests (political compass, attachment styles, etc) do them before the date if possible, and study what the results mean (what the libertarian/authoritarian axis is, or an avoidant attachment style.) Of course, keep in mind that those are just internet tests, not professional diagnoses.

Try to make this not an interview but a "podcast date". The questions provide topics as a starting point and the conversation will eventually drift off, until the current topic comes to a natural close and you can move on to the next question. You'll need multiple dates to get to the end of the list, and that's fine. Just make sure to eventually answer all questions.

Some questions may be too sensitive to answer just yet, especially if you've just met. That's also fine. Take note of these to answer later on when trust is built.

Also consider 36 questions that lead to love as a way of knowing each other. I recommend doing the very basics first (religion, children, relationships) with questions that have the highest probability of being dealbreakers while not being sensitive, then doing the 36 questions, then proceeding with the rest.

You can check the questions you have answered to keep track of what to ask.

Roughly organized from least to most sensitive/personal:

1. Religion

1. Are you religious or spiritual? Why or why not?
2. Is your religion (or lack of) compatible with your partner?
3. What has been your spiritual journey so far and what future do you foresee for it?

2. Children

1. Do you want children? If so, how many and when? Why or why not?
2. Are you open to adoption?
3. What experience have you had with parenting (could be babysitting, younger siblings…)?
4. How will you raise your children in general, especially compared to your childhood? Regarding discipline, education, technology...
5. (If your religious views differ) How do you envision us raising our children under our different religions?

3. Relationships

1. What is your idea of a perfect, healthy relationship?
2. What is your idea of a perfect boyfriend/girlfriend? Which qualities are required and which faults are dealbreakers?
3. What are 5 principles you think are required for a good relationship?
4. How do you view the day-to-day life of our relationship? How often should we talk or do things together?
5. What is the dynamic of the relationship you want? (Traditional gender roles, equal relationship…)
6. Do you believe in the institution of marriage?
7. What do you define as cheating? Is watching porn cheating? Kissing someone else (even a friend) on the cheek/mouth?
8. What are your feelings on sexual exclusivity and monogamy?
9. Do you believe some things in a relationship should be kept private? Why or why not?
10. What are your love languages? (https://5lovelanguages.com/quizzes/love-language)
11. What are your views on friends of the same sex? Do either of you already have friends of the same sex? Are both of you comfortable with that?
12. How many relationships have you had thus far, when, and how long did they last?
13. Why did you break up with your exes?
14. What have you learned about yourself from previous romantic relationships? What mistakes did you make and what did you do right?
15. What is your attachment style? (https://quiz.attachmentproject.com/)
16. How do you feel about your partner quizzing you on all kinds of sensitive and personal subjects?
17. What are 5 reasons why someone would date you and 3 reasons they wouldn’t?

4. Personality

1. Who are the people in your life that have influenced you the most, and in what way?
2. What shows, movies, books etc have made an impact on your life and in what way?
3. What is your MBTI? (https://www.16personalities.com/) (This shouldn’t be a dealbreaker no matter the answer, but helps understand your partner.)
4. What are your interests and hobbies and which ones do your partner not care about or wouldn’t do with you?
5. Would you want to live more rurally or in the city?
6. Ten years from now, where would you like to be emotionally, spiritually, economically, and relationship-wise?
7. Are you more emotional or rational?
8. What parts of yourself would you never change?
9. What is a summary of your life story?
10. What makes it easy for you to be open and vulnerable, and what makes it difficult?

5. Pets

1. What kinds of pets would you be ok with? Dog, cat, rabbit, turtle, goldfish, hamster, lizard, snake, tarantula…?
2. Are you allergic to any pets?
3. Are you ok with having pets while raising children?
4. (If you both want a pet) Who would be the primary caretaker and how would we split financial and practical responsibilities?

6. Money

1. Are you materialistic?
2. How do you handle money? Do you have any problems with money?
3. How would we handle our finances (jointly, separately, both)?
4. Have you ever been bankrupt or close to bankrupt? Are you in debt?
5. What is your employment history and how would it look in the future? How far into your career do you want to get?

7. Sex

1. What are your views on sex in general?
2. How often do you expect to have sex?
3. What are you willing to do? (Oral sex, BDSM…)
4. What is your sexual history?

8. Family & friends

1. What family do you have? How many siblings?
2. Who are your current friends?
3. How do you feel about having friends and family over? How often?
4. What kind of relationship do you want me to have with your family?
5. How important are holidays and traditions to you and your family?
6. What is your relationship with your mother, father, siblings, and extended family?
7. How important is your parents’ approval to you?
8. Do your parents respect boundaries?
9. What type of relationship did your parents have with your ex?

9. Politics

1. Where do you fall on the political compass? (https://www.politicalcompass.org/test)
2. How do you evaluate the next 20+ years of the country you want to live in? Do you think it is overall trending upwards or downwards?
3. Which candidate did you vote for in the last election, if any? (Careful about tribalism. Don’t rule out your partner just because they didn’t vote for your candidate, but evaluate what brought them to vote for them.)
4. How involved are you in politics?
5. What is your stance on abortion and why?
6. What do you think of the Covid-19 pandemic? Did you get the vaccine?

10. Health

1. What is your relationship to fitness and food?
2. Do you have any STDs?
3. Do you have any addiction? (To porn, gambling, drugs, alcohol, video games, social media…) What have you done so far to fight it?
4. Do you have any chronic illness that significantly impacts your life, or any kind of disability (autism, ADHD, infertility, BPD…)?
5. Do you have any trauma? (From childhood, past relationships…)
6. How is your mental health currently?