[Feel free to submit a question for this column, addressing it at massimo at howtobeastoic dot org.]

B. writes: I am 27 years old, already successful, workwise, healthy, well-thought-of and outgoing guy. I have been practicing Stoicism for around a year and it helps me a lot to limit my anger, disdain for many people, sadness, and in general to enjoy my quite exciting, comfortable life. However, there is one thing I can’t get over with and this is my loneliness. I know that as a Stoic I should be pursuing only purity of my character and virtue, the only things over which I have true control, but I don’t enjoy my life just by myself. No matter what I do, from improving my job-related skills to expanding my knowledge, getting fitter, traveling for months only with my backpack to whatever that is considered healthy for mind and body, I have this thought in the back of my mind that I am mostly doing this to attract someone I would consider as worthy of my trust, attractive enough and, most important, smart enough. I know I am very young, nonetheless my few previous, comparatively long and very serious relationships were a huge disappointment for me as I felt alone with all my interests, drive to knowledge and perception of the world. Now, because I don’t want to make such a mistake ever again, I am very picky about my dates, and, well, as you can figure out from this letter, it’s not going well in the course of the normal dating process — always one of us is not “good enough” for the another. It has been like this for around a year.

I just don’t see a point to be skillful and wise just for my own benefit, I have strong urge to share it with someone I trust, and I trust very few people, none of whom are sexually or romantically attractive to me. It happens even though people in general like me and respect me for my integrity and charisma. What should I do?

Take a break, my friend, you are trying too hard. And I say this as someone about twice your age, reasonably successful and well liked (within limits), and with several long term relationships behind me (and a very good one that has been unfolding for the past six years). I’m saying this, in other words, not as much as a Stoic practitioner, but as a fellow man with a bit more experience in this domain. Just slow down, take it easy. It will come when it will come. Meanwhile, though, you have a life to live, so let’s get back to Stoicism.

To begin with, and forgive me for noting this, you seem to be a bit too much into external validation. You write that you are successful, healthy, well thought of; you add that your life is comfortable and exciting, that you travel a lot and do what it is thought to be good for your body and mind. This is all very nice, but of course it falls under the category of preferred indifferents. As Epictetus reminds us:

“Most of us dread the deadening of the body and will do anything to avoid it. About the deadening of the soul, however, we don’t care one iota.” (Discourses I, 5.4)

You only mention in passing that you “should” work on improving your character, which truly is the only thing that matters in Stoicism (and it doesn’t have to do with “purity,” which is not really a Stoic concept). You say that Stoic practice has helped you with your anger and disdain for people, but perhaps you should ask yourself why are you so angry and disdainful? Since you are healthy, young, and successful, what is there, exactly, to be angry about? And why disdain for those less fortunate than you, rather then pity, or — better yet — a positive will to help them? Please consider engaging in some long term self-reflection, for instance by beginning an evening philosophical diary, if you have not done so already, and possibly talking to good (i.e., virtuous) friends, or even a professional, about why you feel this way.

You say that you are doing what you are doing mostly to attract a mate. Needless to say, that is precisely the wrong way to go about it, from a Stoic perspective. You should be nurturing your “soul,” as Epictetus puts it, because it is the most precious part of you, not as a bait to get a date. Again, from the Discourses:

“If from the moment they get up in the morning they adhere to their ideals, eating and bathing like a person of integrity, putting their principles into practice in every situation they face — the way a runner does when he applies the principles of running, or a singer those of musicianship — that is where you will see true progress embodied, and find someone who has not wasted their time making the journey here from home.” (I.4.20)

Seems to me, Stoically speaking, that you are focused on exactly the wrong things. Which may in turn explain why you are unsuccessful at finding someone. Perhaps other people see through your priorities and come to the conclusion that you think of them just as something to accomplish, and they don’t wish to be used as mere means to your own ends?

You write that you have had “comparatively” long relationships that were disappointing. I’m not sure what you are comparing them to, but given your age, they couldn’t possibly have been that long. Are you sure you gave those fellow humans a real chance? Or did you get off the train as soon as a problem arose? Or perhaps when the natural high of initial romance wore off? (Studies show that that period can last to up to two years.) In other words, did you try to do the Stoic thing, i.e., use a problem as a way to practice virtue, turning the obstacle into a new way forward?

“For everything that stands in the way of its activity is adapted and transmuted by the mind into a furtherance of it, and that which is a check on this action is converted into a help to it, and that which is a hindrance in our path goes but to make it easier.” (Marcus Aurelius, Meditations V.20)

You say that you trust very few people, to none of whom you are attracted sexually. Certainly, Seneca does advise us to be picky with our friends, but also to trust them once we select them:

“When friendship is settled, you must trust; before friendship is formed, you must pass judgment.” (III. On True and False Friendship, 2)

That is why I think you should ask for honest advice from a close friend or two, the kind of friend who is not afraid of looking you in the eyes and tell you that you may not be pursuing things in the best way, or that you do not have your priorities straight. If nobody you meet is “good enough” then perhaps you should reassess your criteria, or the way you go about meeting people. When something is not working it seems unwise to insist in going about it the same way. Ask yourself the crucial questions that Seneca says we should pose to ourselves every single night:

“The spirit ought to be brought up for examination daily. It was the custom of Sextius when the day was over, and he had betaken himself to rest, to inquire of his spirit: ‘What bad habit of yours have you cured to-day? What vice have you checked? In what respect are you better?’ Anger will cease, and become more gentle, if it knows that every day it will have to appear before the judgment seat.” (On Anger, III.36)

Notice, incidentally, his mentioning anger, a problem from which apparently you do suffer, and which may be at least a partial root of the situation you are experiencing (together with disdain, which is also very unhelpful when dealing with other people).

I realize that the above may come across as harsh, but my intention is to help, if possible, not to make you feel better. From the little you write it sounds to me like the problem lies inside you, not in the dearth of sufficiently worthy mates out there (I don’t know where you live, but there are currently 7.6 billion people on this planet. Surely…).

So, in practice I suggest the following: (i) forget for now about your quest for a mate; (ii) turn your analysis inward and reflect — better with the help of virtuous friends, or even a therapist — why you feel the way you do; (iii) begin or resume regular Stoic practices, particularly the evening diary, but also simple meditations like the view from above; (iv) re-orient your activities in order not to impress others, but to improve yourself; (v) wait, someone will (likely) come along; (vi) repeat, over and over. Remember that an honest and virtuous attempt to find a good relationship is up to you, actually succeeding at it is not.