Can These 36 Questions Make You REALLY Fall in Love With Anyone?

Posted by in first date success, love after 40 | 0 comments

Remember the viral Modern Love article about the 36 questions that will make you fall in love with anyone? Is it okay to ask them on a first date?


Arielle Ford has mentioned The 36 Questions That Lead to Love on several occasions. According to the study in the article, these 36 questions can make you fall in love with anyone. Arielle Ford says you should ask these questions of strangers on first or second dates. 

What is your opinion? Could it be too personal for date #2?  I recently had a first date with a new man. We had lunch, and for our second date, he wants to go to lunch or dinner again. 

Even though he is very handsome, my gut feeling says that he is still totally stuck on his late wife. She died eight years ago, but he wears his wedding band in his primary Match photo. What? When I confronted him about his photo, he was NOT defensive. He said that he wore his wedding band for five years after her death, and that he joined Match three years ago per his children’s insistence. 

In order to determine IF we are vaguely compatible, do you EVER recommend asking the 36 questions? He is also almost 70-years-old and wants to email or text and NOT have a phone conversation—even though we have already had a two hour first date. Oh, and he talked about himself the entire two hours. He only asked me one question about myself the entire time. 

What is your advice on the 36 questions for our second date? Have you had any of your clients use it early on to determine compatibility?



Can These 36 Questions Make You REALLY Fall in Love With Anyone?


Dear CB,

That first date you described doesn’t sound very compelling. He talked about himself the entire time, and you’re concerned about whether he’s ready to move on after the loss of his beloved wife. You also seem to be annoyed with his communication style of emailing and not calling. Why are you even considering a second date with him?

If you had fun, enjoyed the conversation, and didn’t see any red flags after a first date with a man, a second date could clarify a few things: Was he talking about himself because he was nervous, or is he truly self-centered?

(By the way, a quick tip: if a man talks about himself non-stop on a date, please interrupt him. Ask him if there’s anything he’d like to know about you. Take charge of the conversation instead of feeling like a bobble-head.)

You can also engage him in a conversation to see how emotionally ready he is to open his heart to another woman. I suggest asking what he’s done to heal after his loss. Has he attended a bereavement group or gone to therapy?

In terms of the 36 questions, some are great for a first date, others would scare someone away. I believe that the reason the experiment was successful is that participants knew they were taking part in an experiment. They were not on a date. 

A few years ago, when the study was first published in the New York Times, I asked the man I was dating these questions, and they gave me further insight into who he was. Some of his answers deepened our relationship. And others gave me clarity about why we were not compatible for the long run.

I’ve listed the questions below and highlighted the ones I think would be appropriate for a first or second date. You certainly don’t want to make a date feel like an interrogation!

Which of the 36 Questions to Ask on a First or Second Date?


Set I

1. Given the choice of anyone in the world, whom would you want as a dinner guest?

2. Would you like to be famous? In what way?

3. Before making a telephone call, do you ever rehearse what you are going to say? Why?

4. What would constitute a “perfect” day for you?

5. When did you last sing to yourself? To someone else?

6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

7. Do you have a secret hunch about how you will die?

8. Name three things you and your DATE appear to have in common.

9. For what in your life do you feel most grateful?

10. If you could change anything about the way you were raised, what would it be?

11. Take four minutes and tell your partner your life story in as much detail as possible.

12. If you could wake up tomorrow having gained any one quality or ability, what would it be?

Set II

13. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

15. What is the greatest accomplishment of your life?

16. What do you value most in a friendship?

17. What is your most treasured memory?

18. What is your most terrible memory?

19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

20. What does friendship mean to you?

21. What roles do love and affection play in your life?

22. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?

24. How do you feel about your relationship with your mother?


25. Make three true “we” statements each. For instance, “We are both in this room feeling … “

26. Complete this sentence: “I wish I had someone with whom I could share … “

27. If you were going to become a close friend with your partner, please share what would be important for him or her to know.

28. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.

29. Share with your partner an embarrassing moment in your life.

30. When did you last cry in front of another person? By yourself?

31. Tell your partner something that you like about them already.

32. What, if anything, is too serious to be joked about?

33. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

34. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?

35. Of all the people in your family, whose death would you find most disturbing? Why?

36. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

The questions I highlighted in bold type might help you get to know a man better on a first or second date. Or they might not. I believe that the point of a first date is not to interrogate a man, but to decide if you want to see him again.

Instead of asking a barrage of questions, I suggest you stay present (don’t compare him to any exes), find three things you like about him (focus on the good), and don’t forget to share your passions, too. Be memorable and create as strong a connection as you can.

Whether you ask any of these 36 questions or make up some of your own, have fun and enjoy the journey to true love!


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