The Problem of Friendship

At 54, my pool of ‘real’ friends has noticeably shrunk, while my list of acquaintances and so-called ‘deal friends’ has expanded exponentially. I have no idea what to do with it all, and I want to change that. I have more questions than answers.

Becca Rashid and Olga Khazan’s piece in The Atlantic on “The Misgivings of Friend-Making” discusses the complexities and challenges of forming and maintaining friendships, particularly in adulthood. It highlights various factors that form and affect friendships, like social distance, personal insecurities, divorce, and life transitions. The piece resonated with me deeply. At 54, many of my friends have disappeared due to breakups, geographic moves, kids, or because they, or me, were too much of an ass at some point, and it’s over. Rashid and Khazan’s article reveals a startling fact: on average, we lose one close friend per decade after age 30. With divorce and moves, that number can be much higher (it is for me).

I want to focus intentionally on the challenge of improving my friendships. I’m blogging about it here to start exploring the myriad of questions I have and to recognize the subtleties involved in forming and maintaining friendships — and

I have hundreds of questions. But since 42 questions lead to the meaning of life, here are my 42:

1. What is the best academic research on forming friendships and differentiating friendships from polite social agreements?
2. After several unreciprocated invitations for coffee, when is it advisable to give up and stop pursuing a friendship?
3. Why do friendships often become seemingly less important to people in adulthood — particularly in one’s 50s — and what strategies can counter this?
4. What common apprehensions do people experience before social engagements involving new friends, and how can these be mitigated?
5. How can one combat personal feelings of being uninteresting in social situations?
6. What challenges do adults face in making friends, and how can awkwardness in asking for friendship be overcome? What are some creative methods for forming and sustaining friendships?
7. To what extent should flaws in friendships be accepted, and how can unconditional acceptance be balanced?
8. What methods are effective for resolving conflicts within friendships? When and how is it appropriate to end a friendship?
9. How does geography impact friendships, and how should I think about the predominance of local friendships that characterize most long-term, active friendships?
10. Is investing in new local friendships worthwhile if there’s a possibility of my (or their) future relocation and no school friends are nearby?
11. Should there be a way to recognize when there’s a need for new local friendships if the long-distance ones are no longer reciprocated?
12. Is it practical to view friendships as an asset portfolio, focusing on acquiring local friends in each case (as these are frequently the highest value)?
13. Under what circumstances and in what ways should I spontaneously contact a potential friend without prior planning?
14. How can Arthur C. Brooks’ concept of ‘deal friends’ transition into ‘real friends’? How can deeper friendships be developed from acquaintanceships?
15. How should potential friendships connected to past life projects (e.g., professional engagements) be approached after the formal engagement ends?
16. How should the end of a friendship be discussed with our mutual acquaintances?
17. Are there differences in male friendships with women compared to men, and what are they?
18. What are indications that a friendship with the opposite sex might evolve beyond platonic, and can it be preserved?
19. What ethical considerations should be made when pursuing a friendship with someone who seeks only platonic interaction while desiring more?
20. What considerations are important in friendships with gay friends of the same or opposite sex?
21. When discussing one’s love life and dating, how can this topic be navigated without knowing the tolerance for a friend to discuss such things?
22. How do I ask a ‘deal friend’ or even a ‘real friend’ what they need in a friendship and what they dislike or don’t?
23. What is the appropriate way to develop an interesting friendship with a friend’s friend?
24. How should friends be approached for roles reserved in our society for love interests, like emergency contacts?
25. What are my personal qualities that enhance my friendships, and what are some techniques to be a better friend?
26. What strategies effectively maintain friendships that may always be at a distance so they remain robust when needed?
27. How should I consider the time and effort spent maintaining ‘deal friends’ vs ‘real friends’?
28. Is it acceptable to use a personal assistant to send birthday and holiday acknowledgments due to personal difficulties with remembering and acknowledging these occasions?
29. How should the evolving relationship with one’s children from parental to friendship-like, be navigated while maintaining appropriate boundaries?
30. Can a real friendship exist despite trust issues, and if so, how can this be addressed?
31. If a love interest isn’t a close friend or fully trusted, should the relationship be reevaluated, and does a lover need to be a best friend?
32. Is creating a tracking system for interactions and important events with friends a useful strategy?
33. How can one recognize and respond appropriately to someone else’s effort to deepen a ‘deal friendship’ into a ‘real friendship’?
34. Considering Tim Ferriss’s idea that we are the average of the five people we spend the most time with, how can I effectively apply this ‘Ferriss Rule’ to assess and cultivate my friendships?
35. What specific qualities should I look for in friends according to the ‘Ferriss Rule,’ and does this imply a different approach to acquisition compared to how friendships typically form in younger years?
36. Does the ‘Ferriss Rule’ suggest that having around five close friends is ideal, and should this number influence the selection and maintenance of my social circle?
37. How do different cultural backgrounds influence the dynamics of friendships, and what can be learned from cross-cultural friendship experiences?
38. In the age of social media, how does one navigate the distinction between online friendships and in-person relationships?
39. Is an online friendship a new category of friendship that’s worth maintaining? How?
40. How do major life changes like job changes or being a single parent affect existing friendships and forming new ones?
41. What role do shared hobbies and interests play in strengthening friendships, and how can one find friends with similar passions?
42. How can friendships contribute to personal growth and self-discovery (e.g., seeking friends from opposite political perspectives), and what strategies can be used to cultivate enriching relationships despite values differences?

I don’t expect to answer all of these questions, but for now, they guide my inquiry. Let’s see what I find.