The Fussy Suitor

“Optimal stopping” is a thoroughly studied problem domain in mathematics. It is concerned with the best time to take some particular action in order to maximize some expected reward. The most famous instance is the fussy suitor problem (otherwise formulated as the secretary problem or the best choice problem): you are a bachelor type, trying to pick a suitor as your forever partner. You can only date one suitor at a time, and once you reject them, you cannot date them again. Once you choose one, congratulations, <3 you’re done with the bachelor life.

If you want to step aside momentarily to think through a solution to this problem, this sentence is your opportunity to do so because the next sentence has the solution. Assuming random ordering of when you meet the suitors, the odds of picking the best possible suitor are maximized if you date and reject the first (1/e)~36% of suitors then pick the first next one who is at least as good as the best one dated so far. So if you have N suitors total, date and remember the best of the first 0.36*N and select the first of the remainder that meets or surpasses that bar.

My most recent bout with romance ended this week, and in my disappointment, I thought, “what if this is my N?” Should I have followed the mathematically-optimal solution? I thought through previous boyfriends, lovers, partners, flings. C’est la vie to Celine’s high school and college picks in the early 36%. I mentally step forward in time, and I suppose I know who would be my first-best-of-the-remainder. I imagine we could be happy together now, but something is unsettling. I wonder if maybe, since we’re talking about random ordering, some other order of life experiences would yield a better-feeling result. I imagine the reverse direction– goodbye to the most recent and hello to younger flings. Gosh, that also feels weird– to progress into romances from a younger Celine with younger ideals. The failures and the successes embedded within them have over time formed my reality, and in imagining an alternate reality I almost mourn the Celine I have grown to know.

So why does the mathematically optimal solution feel so wrong? (Reader, I bet we could come up with a million reasons that have to do with the flexi-rigidity of human souls, but I’ll offer something more precise…) The assumption is all wrong: chronological is not random ordering. The deep intertwining of
relationships, affection, perception, and mistakes with time
touch my life line to adjust my
values, expression, outlook, and self-ownership with time.

So we find ourselves with this lens that adjusts its focus for optimality over time. The optimal stopping problem now feels more confusing with both the reward-measuring tool and the options changing with time. But I think it remains quite simple: if both are randomly ordered, we can still follow the 36% rule. Alternatively, we should hope (and we can try our best to make this close to true in practice) that the reward-measuring tool follows a general trajectory of improvement alongside yourself. The suitors, the love and the angst and the uncertainty and the space they occupy blend to tune the measurement.

In this view, the problem of the fussy suitor was never about the suitors. It’s about the singular fussy suitor. And it is formulated as follows: you are an individual, sharing love and finding yourself through vulnerable experiences. In a given reality, you can only live one life line. How does it look?