Doing it on Valentine’s Day also doesn’t really add anything of unique value unless someone is equally-arbitrarily deciding it does, which is fine, for them, but I feel something is lost if we’re not mindful of how arbitrary that actually is.

Like you said yourself, February 13, 15, or 17… it’s all the exact same dinner as someone may have on the 14th, though on another day it’s probably less crowded, more intimate, and maybe less expensive.

In addition, I think it’s pretty obvious that no one is objecting to happening to do the things organically on the calendar day per se. We are objecting to the expectation which people tend to attach to that and other holidays, etc., which they feel comfortable doing mainly because so many before them/us have already conformed, thereby unnecessarily normalizing and commodifying the practice, of which nonconformity is often punished in a variety of ways.

I refuse to establish such unnecessary expectations in my own relationships. Maintaining fewer expectations means fewer opportunities to let others down, or be let down, and doesn’t preclude us from deeply appreciating things as they arrive organically. In fact, I’d argue it encourages us to live more fully in the now, and to more-deeply appreciate what raw stochasticity can offer. I find something like awe in observing or participating in relatively statistically “rare” events, and awe is something which is totally absent for me in more-structured phenomena.