I Asked My Best Friend to Fall in Love with Me
25 questions to build connection and understanding — for partners and friends.
“Hate is a strong word “, a phrase my mom used far too often growing up, so much so that myself and the rest of my family have inevitably committed it to memory. It’s a sentiment only my mom holds, however my sister has never been ashamed to snitch and bask in the satisfaction of hearing my brother and me getting scolded. Then and now the word remains an obscenity in our home. So, since I fear the repercussions, I say it sparingly that I hate distance, and though I was once fascinated by the concept, I also hate time zones. Sorry, mom! And since my friends’ recent move to London, we’ve become victims of both. While it’s definitely not our first choice, it has become our norm to video call as often as we’d typically meet up for food, or a movie, if she were not halfway across the world. It’s a luxury we routinely indulge in an attempt to not only break the humdrum of our busy lives but also to connect and catch up. Admittedly, a video call is much less fun than driving a golf cart on some remote South African farm and playing music together, but we’ve made do with as best we can.
Two weeks prior to our call, I had been browsing through a popular publication that had published an article of 36 questions that they believed could cause any two people to fall in love, (or at least come close). Of course, I was intrigued and lightly glanced over the questions. I intentionally decided to not give much thought to any of the questions, because I was determined to sit down with a friend or potential partner at some point and answer them as genuinely as possible. Hold this thought for a second, we’re going to come back to it soon.
Anyways, Lily (we’ll call her Lily for the purposes of this article) and I got into conversation and though we do converse regularly, I felt as if there was a mutual excitement to “see” each other on our devices. As per usual, the conversation was mainly just laughter and stories to share, but the tone changed a little bit as we began to speak about what was bothering us. In an unprecedented way, we were almost at identical crossroads in our lives that were marred by a mix of uncertainty, transition, and a fair bit of anxiety. We were both quite unsure of what steps to take and though we both couldn’t seem to figure out our respective circumstances, so we decided to channel our inner Jordan B Petersen and try to psychoanalyze each other whilst offering advice.
I found the positive nature of the moment to be an opportune time to ask Lily if she wanted to do “the questions” with me. Of course, I had to preface my question by reiterating that I intended for this “exercise” to be purely platonic, I didn’t want to give her the same shock her childhood best friend had recently when he had suddenly professed his undying love for her, and willingness to ditch his father’s “plaas” (Farm) and join her in London. Fortunately, Lily had no reservations whatsoever, so she pulled out her rose gold MacBook, and I subsequently pulled out my much less glamourous laptop and we began to alternate asking each other questions.
In the end, we found ourselves both naked. (Not literally, get your mind out of the gutter). We had answered close to fifty questions in by far one of the most candid, vulnerable, and open conversations either of us had ever had. We were both bare, we had laid it all on the proverbial threshing floor. From death, to love, ambition, and fear — we’d seemingly left no stone unturned. It was as if we’d lost sense of everything going on around us, we were about three hours into our communion by the time we had finished these questions, and I certainly didn’t anticipate that we’d exchange such inward and intimate thoughts. I’d even forgot about my two-minute microwave popcorn that was on my desk, and if you know me, that takes a lot.
I guess you’re probably wondering, did we fall in love? Well, there’s no good story without a sequel, or as the great Kenny Rogers put it, the secret to surviving is knowin’ what to throw away, and knowin’ what to keep, so perhaps you might want to hang tight for another week or so. If she does though, you’ll have to admit I’m a total stud.
But seriously, whether you intend to cast a spell that will help you escape the friend zone for good or simply reach a more intimate connection between friends or family members, these 25 questions will help you do just that. I compiled these questions from a range of sources. Some of them include the original set Lily and I answered, ideas and themes from my psychologist Ilze Alberts’ blog, and the majority are questions I put together. Try asking these on your next date night, facetime catch-up, or at your next awkward family gathering.
25 Questions
Part 1
1. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
2. Name one trait you admire in your partner?
3. What is your earliest memory?
4. How can love or affection best be expressed to you? As a guide, Gary Chapman theorized that there are 5 Love languages; words of affirmation, quality time, gifts, acts of service, and physical touch.
5. What roles do love and affection play in your life?
6. When your life is over, what do you hope to have accomplished?
7. Complete this sentence: “I wish I had someone with whom I could share … “
Part 2
8. Is there anyone you hold a grudge against? Why haven’t you forgiven them?
9. If you were to wake up today with only what you were grateful for yesterday, what would you have left?
10. Take four minutes and tell your partner your life story in as much detail as possible.
11. What single event changed the trajectory of your life?
12. When your life is over, what do you hope to have accomplished?
13. Do you believe in a higher power, God or Deity? If not, why not? If you used to, what changed?
14. What are your non-negotiable needs in your relationships?
What are the things that are essential for you to receive, and on the contrary, what are the things you are willing to give?
15. Given the choice of anyone in the world, whom would you want as a dinner guest?
16. What do you value most in a friendship?
17. Make four true “we statement” each. For example, “we are both in this room feeling … “
Part 3
18. Do you believe conflict is an essential and beneficial part of relationships? Can two people truly be content/free in a relationship where they avoid conflict?
19. What meal can you cook like a world-class chef?
20. Do you have any intuitive feelings about how you will die? Do you mind sharing?
21. Share your true feelings about your partner. (Express gratitude, grievances, issues); be sincere and be vulnerable
22. What are your beliefs around money and relationships? Should the two be mixed? Can unpaid debts sour a relationship?
23. You get to participate in an Olympic event of your choice? What would you choose?
24. What is your relationship like with your family? What about your childhood would you change?
25. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect to you on how you seem to be feeling about the problem you have chosen.
Bonus Question: Is water wet?
Sources
https://www.nytimes.com/2015/01/09/style/no-37-big-wedding-or-small.html
https://www.jordanbpeterson.com/blog-posts/on-the-psychological-and-social-significance-of-identity/
https://www.ilzealberts.com/turning-point-a-journey-of-self-discovery-awaits/
