You’ve sown your wild oats. You’re ready to settle down. You have made a conscious decision that security is more important than novelty, that you will grow more in a committed relationship than by random dating.

But it’s 2024 and it seems as if everyone is perpetually looking to trade-up, to find more, better, different on an app, if not at the gym or in a cafe or club.

Below is a list of 40 things you need to learn about the person you are dating to find out if you should marry them. Essentially, you can think of this list as a psychotherapist’s way of reverse-engineering a marriage after witnessing so many crash and burn.

1. What is their intention?

Be 100% certain that the person you are dating truly would like to get married and find out WHY they want to get married. If it is because they are lonely and desperate or because all of their friends have gotten married then they may not be aligned with your intentions. Do they think they are ready for such a commitment? Do YOU think they are ready for that commitment?

2. Are they age appropriate?

This does not pertain to actual number of years someone has been on planet earth. This question is really “Do they have similar life experience(s) as you do?” Familiarity does not breed contempt when getting married. Of course there is a certain eroticism to exoticism, but having grown up listening to the same bands or watching the same shows gives you a shared vocabulary.

3. What are their beliefs about monogamy?

Do you mind if they are still on dating apps if/when you begin having sex with them? Do you mind if they are currently dating several people? What is their definition of monogamy? Do they consider virtual flirting — DMing shiny objects on IG — breaking the covenant? Seriously, this may surprise you but everyone has a different definition of monogamy and when forming a couple the individuals should have an overt agreement about what behavior they will and will not tolerate. Assume nothing. The map is not the territory.

4. What is their marriage/engagement history?

Why didn’t their past relationships work out? I don’t believe there should be red flags here if they were never married or married eight times. On the other hand, you should note any patterns and be comfortable with their explanations about the break-ups. Definitely take note if your potential partner appears to be some sort of magnet for narcissists, borderlines, or any series of mentally ill exes.

5. What is their timeline?

In an ideal world WHEN would they like to get married? Do they have career goals or a certain age that they would like to attain first? Do they think that living together before marriage is a good idea? For how long? Be sure that the two of you are aligned with WHEN you both would prefer to be wed. Do you agree on how long people should date before getting engaged?

6. What are their thoughts on having children?

What are their desires and expectations regarding having children? How many would they like to have? How soon? Are you on the same page regarding child care and if you are having children who will take care of them and for how long? Also, you may want to ask if they already have children with a someone else.

7. What is their emotional intelligence?

Do you feel that they have a similar level of emotional intelligence and maturity to you? Do they know how and when to shut up and empathize? Marriages shouldn’t be therapy, but they are therapeutic. If your partner fails to attune to you and is jokey when you’re grieving it means that they don’t have the emotional intelligence to attune to you appropriately. Knowing how to validate your partner’s emotional experience is a key to a healthy marriage (sometimes even when you disagree with them).

8. What is their lifestyle?

Urban, rural, how many times per week do they like to dine out? What type of restaurants? Do they like to cook? Do they like to entertain? Are you two on the same page when it comes to sharing time together and having fun?

9. What activities do you share in common ?

Do you have enough common activities that you enjoy doing together? Sports, hiking, yoga, meditation, cooking, classes, etc.

10. What are your shared entertainment interests?

Do you enjoy similar types of concerts, movies, theater, music, books, shows, art?

11. Do they have individual passions?

Do you and they have sufficient separate interests so that neither of you are completely dependent on the other person during free time?

12. Do they seem like they would be the type of friend you would want to have?

Can you imagine that the person you are dating would be a good friend, a pleasant companion? Someone to do fun things with even if the romance weren’t there?

13. Are they on the same page about romance?

Are you two on the same page about what “dating” looks like and what a “date” is? Do you like the same type of venues? Do you agree on what a “date” is and who pays? What constitutes a “date” or are you both OK with just “hanging out”?

14. What is their friend group like?

How quickly or slowly do you each think you should introduce each other to your friend groups? Do you like each other’s friends? Are you OK with the number of friends they have or lack thereof?

15. What types of relationships does your potential partner have with their family members?

16. What types of relationships does your potential partner have with their ex-partners?

17. Money.

Do they have similar levels of financial stability and income? What type of monthly commitments do they have and for how long? Student loans? Credit card debt? Mortgages? Car payments? Health Insurance? Etc.

18. Are you two sexually compatible?

Are you physically attracted to each other to the same degree? How often do they want to be intimate? What do they consider to be “normal” in terms of sexual activities and do you have similar levels of adventurousness or lack thereof?

19. STDs.

This is a difficult subject. There is no right or wrong answer but a lack of transparency could later register as lying or betrayal so no matter how embarrassing or unsexy it may be, everyone should lays their cards on the table as early as possible.

20. Alcohol, drugs, smoking.

Do you have the same attitudes about alcohol, drugs, smoking? Have they ever had a problem with alcohol and drugs?

21. Do they have any past or current legal issues?

Have they ever been arrested? Are they amidst any lawsuits or legal battles?

22. What is their work/life balance?

Does it seem as if they have the right balance of work time and leisure time? When they are not working how much time do they spend in front of a screen (on social media, playing games, etc.)? Are they able to detach from devices or are they constantly reaching for their phone?

23. Pets.

Do they have pets, if any, and how much time and attention do they give their pets? Do their pets sleep in their beds? Do they have to rush home from dates to walk their dogs or feed their iguanas?

24. Vacations.

Where have they vacationed and are your vacation styles similar? Do they appreciate the same type of accommodations that you appreciate? Do they like to sit on a beach or stroll through museums?

25. Mental health.

How severe is their trauma history? Are they on any medications? How are their moods — do they tend to trend melancholic or happy? History of depression? ADHD? Anxiety? Are they in therapy? If so, what issues are they working on?

26. Physical health.

Are they healthy? What do they do to be healthy? Do you have similar exercise regimens? Can you go to the gym together or find some way to exercise together?

27. Do they know how to fight/argue/disagree respectfully?

Do they know about the Gottman’s 4 horsemen that destroy marriages — contempt, stonewalling, criticism, and defensiveness — and how to avoid them?

28. Can they communicate their thoughts and emotions authentically, compassionately and directly or do they act passive/aggressively until you pry their thoughts and emotions out of them?

29. How do they treat strangers, salespeople, waiters?

Are they polite? Generous?

30. Personal hygiene, how they dress, and how they present themselves.

Do you two have similar understandings of what it means to be “clean” or at least “presentable”? Do they agree on what it means to “dress up” and look presentable for specific occasions? If you invite them to a professional function would they know how to dress appropriately or at least ask you what they should wear? Do they put an effort into being clean when they are coming to see you?

31. Are they into personal growth?

How do you each respond to suggestions or light criticism? Have they done their emotional homework? Are they willing to make adjustments?

32. Congruence.

Do their actions match their words or are they disingenuous? Do they have personal integrity and show up to dates and functions on time?

33. Materialism.

Do you have the same attitudes towards material possessions? If one drives a Lamborghini and the other drives a Hyundai will this affect how you feel about each other?

34. Home cleanliness, order.

Notice the level of cleanliness in their home. This shouldn’t be a dealbreaker but if you peek into their closet and it looks and smells like a bomb exploded then you may need to politely ask them to up their cleaning game.

35. Communications via technology.

Do they like to engage in conversations via text or DMs? Do they prefer to speak on the phone? FaceTime? Do you notice that they only call you when they are in their car? Are there specific times during work when they have established that they will not be available to speak or text? What are their rules regarding how they like to interact via technology and how many times per day is acceptable?

36. Social media.

Do you approve of their social media, who they follow and who follows them? What’s their definition of monogamy (if that is what you have agreed upon)? How do you feel about them having virtual relationships and flirting online with strangers or exes via social media?

37. Politics.

On the spectrum from conservative to liberal are your views somewhat similar and, if not, can you respectfully “agree to disagree”? We are currently living in a very bifurcated political arena wherein political disagreements often devolve into attacks on one’s personality and intelligence, each person thinking that anyone who disagrees with them must be “ignorant.” Can you discuss differing opinions calmly or are your views so disparate that it pains you to be around someone with their ideology?

38. Religion(s).

How committed are they to any religious beliefs and do those beliefs align with yours? If you decide to have children together what faith — if any — would you like them to be taught? Christmas, Hanukah, both or neither? Are there any family obligations such as Easter or Passover that are super important to either your or their parents? Do you respect your potential partner’s faith or would you prefer if they at least experienced some other type of spirituality?

39. Effort.

How much effort are they willing to put into a relationship? What type of work are they willing to do in order to make the relationship work? Do they understand that relationships require fairly constant maintenance and that marriage isn’t the finish line, it is actually the beginning of a marathon.

40. The wedding.

Do they want a big or small wedding? Do you agree on who should be invited and why or why not?

As I mentioned in the introduction, the above list could be viewed as 40 discrepancies that I have witnessed destroy marriages, that if this information came to light while the couples were dating that they may not have gotten married and thus avoided the often bitter pain of divorcing.

In the future (like when a tech developer or calls me), obviously there will be an app that instantly gauges and scores marital compatibility and explains discrepancies and/or dealbreakers. I am sure online dating services already have complex algorithms that calculate how much two people have in common. However, dating compatibility and marriage compatibility, from my perspective, require two completely different skill sets. It is clear to see that the rapport/trust building process in dating is at odds with the authenticity/transparency part of dating. Both have to unfold organically; neither can be forced. If someone goes on a first date with my above checklist of questions in hand they would scare the bejesus out of their date. On the other hand, if you wait until you are living together to find out if your partner has ever been arrested or is still enmeshed with their ex, then you have waited too long. It’s a dance. And too many people prefer to be swept up in the myth of romance (chapter 4 in “How To Survive Your Childhood Now That You’re An Adult”) when dating to marry. Pray you, avoid it.