25 Questions That Might Help You Fall in Love Again

Not long after Casey and Meygan Caston married some 21 years ago, they found themselves feeling disconnected and disillusioned with their relationship, and almost called it quits. “We fought over everything,” says Casey, 46. “We were really hurting.” Not willing to give up, they began some hard work that led in 2018 to a self-published book, 365 Connecting Questions for Couples, listing a year’s worth of open-ended questions designed to get romantic partners talking and deepening their bonds.  ​

​“In modern days, we’ve lost the art of asking really good questions,” notes Casey, who lives with Meygan, 42, and their two teenage children in Southern California. (The pair also founded Marriage365, a “marriage-solutions company,” offering relationship courses, coaching and such.)​

​The book sold 100,000 copies within five years. Now they’ve come out with a revised version, swapping out 200 of the old questions with new ones, based on feedback from readers and discussions with hundreds of couples who used the book. Some questions are likely to stir the pot a bit (“How many times have you been in love? Tell me about it.” Um, check please!); others are just kind of fun, like, “If a movie were being made about us, who would play you and me?”

“Make it work for you and your relationship,” Casey suggests. You can try to tackle one question a day, but “a lot of times couples will binge a bunch at once.”

​We worked with the Castons to find 25 questions likely to be most relevant for people who have been together for many years. Among the 25, Casey notes, are “some we’ve heard were helpful over and over again from our couples who are older, and some are favorites for our own marriage.”​

​But, in a way, it’s not about the questions: It’s about being curious about and present for the other person. ​ ​

25 questions for reconnection​ ​

1. Who was your childhood hero and why?​ ​

2. If you could pick one year of life to do over, which year would it be and why?​ ​

3. What are some ways you would like to have more fun in our relationship?​ ​

4. If you could build your dream house, what would it look like?​ ​

5. If you could talk to your teenage self, what would you say?​ ​

6. What do you think is the best and worst thing about getting older?​

7. When you come home from work, what can I do or say that will make you feel the most loved?​​

8. Do you think it’s okay to break the law if there are extenuating circumstances? Why or why not?

9. What does our ideal sex life look like for you in this season of life?​ ​

10. Which of your five senses do you think is the strongest? Why do you think that?​