Valentine’s Day & The Lessons Of Perpetual Singlehood

Kelly Fleming
Inferno
Published in
6 min readFeb 14, 2021

Alone with a bottle of merlot and a bag of pink Hershey’s kisses is, for many women, what Valentine’s Day looks like. It is not a thing to be ashamed of, but it is a reflection of what seems to be a growing disparity between the desires of men and women in relationships.

Illustration By: Kelly Fleming

We can do the personal growth exercises, we can paint the picture of a relationship we would like to establish in our minds and we can even discipline ourselves as to not expect these things right away from the potential mates we meet in person, to be both patient and kind with them as we should be. But the crux of this seems to never be the amount of self-awareness we’ve built or the time (and money) we’ve spent making our bodies and minds attractive enough for such a suitor. It seems that the crux of this is the tendency for male counterparts to desire singlehood while many women humorously dread it. While, for them, singlehood has been equated with freedom and endless choice, for us it seems to be the opposite, at least when it becomes something we’re very, very used to.

That is not to undermine the benefits of female singlehood, it is to point out the difference between singlehood and perpetual singlehood. Women (rightfully) take ownership of their singlehood, find a kind of freedom in that and can have enormous amounts of fun being single, especially while young. But being perpetually single is a completely different story and, it might be, a completely underestimated phenomenon that makes people callous towards relationships and turns relationships into transactional situations that cannot possibly become deep enough to benefit either party significantly.

Singlehood, As Our Generation Understands It And Misunderstands It:

Being single in your twenties is a relatively new cultural phenomenon that has sparked many misconceptions about dating as painted in the media landscape. These misconceptions about singlehood are the cause of great miscommunication and, at the individual level, much more difficulty in making a personal decision to either remain single or to even bother trying to find a partner.

Singlehood is an opportunity for personal growth and optimism, much like that period during college when you’re still deciding what you want to do with your life and it has not been met with the dread of taking the first step in pursuit of such desire. Yes, at its best, singlehood is a chance to be unashamed of one’s identity and to allow it to grow into an attractive aura that eventually reels in other attractive prospective partners.

At its worst, though, singlehood is a chance to beat the living hell out of oneself with the bitter truth that no prospective partner has yet taken interest in us. If it is a chance to be totally unashamed of our identity because there is no significant other to tell us there is something wrong with it, then it must also be a chance to drown in shame of our identity because there is no one there to offer a positive feedback for the things we have to offer.

The truth underlying these things is that it is not singlehood itself that ought to be understood but the cause of it. One psychological misconception we struggle with is that looking at something we are ashamed of will magnify that shame. The reality, though, is that ignoring the aspects of ourselves we are most ashamed of is the thing that magnifies them in our unconscious while simultaneously rendering them unfixable.

Singlehood As A Result Of Unresolved Trauma & Low Self-Esteem:

Of course, it is not enough to just get angry with the state of manhood in modern times. It could be well asserted that the reason why men are chronically afraid to commit to women (even if marriage or “serious relationships” are not in the question) is a special type of anxiety that women cannot relate to. Surely, eligible bachelors must feel the same sense of longing for a stable mate that young single women do, if only at a subconscious level that is drowned out with hedonistic distractions that we have readily available.

No, to be a single female at this age and to do it correctly requires a degree of introspection that most aren’t willing to delve into. One must understand all the things that play out and play out again when dating someone new. That is, a new relationship can shed light on needs that we didn’t even know we had and wounds we didn’t know still needed to be dressed. For women who faced complications with past relationships or even their fathers, negative perceptions of men in general are a barrier, and no small one.

All relationships, even non-romantic, serve us as reflections of the dialogue that is playing out internally. If we are engaging in a relationship that causes us much disturbance and becomes triggering, it feels right (and often, technically is) to look at the other person as the villain. But it is simply not good enough to do that. We must understand the internal dialogue that plays out constantly within the confines of our own pscyhe, and in the same way that a sad song or a movie can trigger emotions that were already inside of us, understand why painful moments in relationships do the same.

How to Navigate Constant, Low-Grade Rejection:

Rejection is, at its best, a catalyst of self-improvement.

The pain associated with rejection exists on a spectrum, of course, not all are well-equipped to deal with it. For some, it is merely a mismatch of space and time that had nothing to do with their worthiness of love and for others it is just those things and it then becomes a reinforcement that love can never manifest.

If you are one of these individuals who takes rejection well, then you are probably much closer to finding love than those who are crushed at the mere “mismatch” on a dating app. And while, if we are being honest, there are going to be people who are probably not attracted to you, people who do think negative thoughts about your appearance and personality, the cognitive dissonance required to see this correctly and to still believe that you are worthy of love is the secret ingredient to finding it.

Yes, the cognitive dissonance of seeing that some people you like will not be attracted to you or want to be with you and still think that you are worthy of a partner who is attacted to you and wants to be with you is (I think) the secret ingredient.

But it is exceptionally difficult to build this cognitive dissonance if you suffer from low self-esteem, and this is why we must delve into this emotional pressure point to develop to right mindset to navigate perpetual singlehood. To not believe that you are worthy of finding love is to never put yourself in a place to find it. To not believe you are worthy of finding love and to grow angry and resentful from this self-limiting belief is also to keep yourself from finding it. And it is these two extremes that are incredibly difficult to avoid while we navigate. It is incredibly easy to turn to self-destruction at the belief that we are unworthy of love and particularly easy when low self-esteem prevents the brain from being able to isolate incidents of rejection and grapple with them as the small, relatively insignificant moments they are. Rather, when rejection pairs itself with an individual sufferring from low self-esteem it gains a momentum that quickly turns ugly and, sometimes, can snowball into retrogressive and self-destructive behaviors.

Where is there room for optimism here, if we are to accept the less-happy of these two truths? How can we accept that even though there has been a rejection, a mismatch of time and space that has caused us to be single, that it is not a reflection of our inability to be a match to anyone? Well, ultimately it would be to understand it as a call for us to embody the characteristics we’d look for in a partner ourselves. At the very least we could come to convince ourselves that we deserve to be in the presence of kindness and succes, whether or not it is generated by someone else. And if we could learn to, as single people, be the match we want to make someday, then it is inevitable that it will happen and it is also impossible that we would ever bring ourselves to settle for less.

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