The Real L Woes: The Pitfalls of Modern Dating



Sometimes I wonder if I’m going to die alone—”sometimes” being loosely defined as “regularly” — because life is unfair, and dating can often times feel impossible. Waking up to your dog’s morning breath, taking showers alone and scrolling past loving couples kissing in your Instagram feed serve as daily reminders that you’re solo, and that there’s a good chance you will stay that way indefinitely. And while I can’t speak for previous generations of daters, seems modern dating has become a meandering processes of head games, dejection and waiting around for the next best thing. Is it possible to create a meaningful connection without feeling completely worthless and insane?

From my experience, no, especially with social media having a hand in how we communicate with one another. Dating in today’s world is comparable to an extreme sport. Thinking back, I find it almost endearing that my Lion King emblazoned diary was a tome of all my unrequited love yearnings, wanting nothing more than to find acceptance thorough love. Problem is, as much as I like to think of that as a thing of the past, reality tells me that things haven’t changed. From that diary to a 30-something-year-old reality, I now face the fact that this shit is exhausting and that I spend an obscene amount of time dating and subsequently obsessing over what is wrong with me.

I recently vowed to give up on dating for a year to concentrate on reclaiming my self-esteem, which was at an all-time low, but as a hopeless romantic, an idiot, or just someone who’s addicted to the idea of love, I gave it another shot. Having met someone I genuinely liked who liked me in return, I felt like I was finally living a fairy tale. And then I remembered:


So enough, I give up! I’ve never been afraid of putting myself out there, but at what cost? The only kinds of relationships I’ve successfully maintained are one-night stands and weeklong relationships, the rest being nothing more than prolonged bouts of insecurity-induced delusions of grandeur. Having just celebrated the first anniversary of my 30th birthday, I have become well versed in some of the pitfalls faced in the modern dating world.

I can’t even be sure the “old-fashioned” dating even happen anymore. You know the kind I’m talking aboutgetting cruised from the other end of a bar, engaging in a discussion of which far more attractive celebrity you’ve been told you look like, all being enabled with alcohol and mild desperation. You’ll probably forget her name but will always remember that evening as the time you had sex with Tom Cruise.

Nowadays, it’s far more likely that Tom would’ve been too busy swiping through her Tinder than actually looking up across the bar. Dating online has made its way into the fabric of normal courtship and has since monopolized the market. Back when I started, all we had was Craigslist. From online dating to dating apps, the detached forms of forming connections have all but ruined ones chances at finding deep connections. Social media has also created the illusion of having endless options, which perpetuates our waiting around for the next best thing. Finding someone willing to focus on one relationship at a time has become challenging, or damn near impossible.

Very few single people are content with just courting one person at a time. I’ll translate, courting is an archaic term that is defined as being involved romantically, typically with the intention of commitment. So many people are scared of commitment and being official that they remain in label-free relationships with multiple people, continuing to flirt and keeping multiple romantic interests or exes on the side. There are also plenty of people, predatory in nature, who’ll have no qualms overstepping boundaries to pursue your potential love interest. This blurring of relationship lines has led to mainstream dating culture bastardization of the polyamory lifestyle. Sleeping around and covertly dating more than one person does not a polyamorous relationship make. In actuality, the first rule in Polyamory Club is open-communication. Appropriating the term when actually just “playing the field” is uncouth, and leads to used people and hurt feelings.


That’s not to say that there’s anything wrong with wanting to keep things casual. No Strings Attached isn’t only a life-altering ‘N Sync album, it is also a legitimate way to date. Unfortunately, to the untrained eye, these folks will often look the same as anyone else and they won’t always tell you their true motives. Instead, they’ll eventually excuse themselves from the situation with an, “Oh I wasn’t looking for anything serious,” or “Sorry, I’m too wounded,” and you’ll never hear from them again. Turns out, you can spell dating without honesty, even when the text they sent started with, “If I’m being honest…”

The effortless cool, blasé attitude that has been plaguing our generation since the dawn of hipsters has seeped into how we relate to one another when dating and now, the person who is able to act the most aloof holds all the cards. If you show too much interest you’ll look desperate, but showing too little makes you seem uninterested. A person acting distant while intermittently showing signs of genuine interest is confusing, but is probably the closest you’ll come to actual validation.

Because of this culture, psychological games like counting the days before you text and being led on are becoming the norm. While it makes more sense to by upfront and honest with your feelings, those who do are the fools who’ll find themselves waiting for texts and obsessively checking to see if their phone accidentally flipped into airplane mode.

We overextend ourselves socially to potential love interests as a way of avoiding doing the hard work to identify our actual feelings. We’ve also become afraid of hurting someone else’s feelings when we’re simply not interested, by saying what we think we should say instead of what actually need to say. While often times unintentionally, this allows the relationship to go on far longer than it should have, more commonly leading to someone getting strung along.

Being indirect is the language of modern dating. However you first met, chances are that most of your initial communication will happen via text, a seemingly direct option but actually one of the most impersonal. A simple “let’s meet” is vague, and could mean any number of things. Making plans is a lost art form. Thanks to technology, there’s a good chance you’ll find yourself in a perpetual land of waiting, the most decisive response you’ll get being a “maybe” or an “I’ll let you know.” Make no mistake, dating has become a game of options, the deciding factors being if you are more interesting than whatever events are popped up on Facebook that afternoon.

That all being said, being proactive can often times be misconstrued as creepy, depending of course on how attractive the other person finds you. If you are an open and honest person, or at least someone who does their best to be upfront, you’ll most likely be looked upon as someone who’s too interested, and therefore desperate because, heaven forbid, no one wants to be the one who openly admits to liking someone. It also leads to mistreatment within relationships. Not only do you not want to seem interested, but we’ve also created a false pretense that the person you’re dating is replaceable. Being passive aggressive and patronizing to ease feelings of insecurity and doubt are just a few of the common issues that plague budding relationships.


Because of our aversion to confronting things head on, getting dumped will most likely be via email or text to avoid having to physically deal with having hurt another person. Without having any sort of explanation, it may also feel like a devastating dance of trying to figure out what went wrong. It’s rare to find someone who’ll be considerate enough to talk in person, and even if they do, it’ll most likely be a lot indirect reasons, perpetuating a wealth of self-doubt and insecurities. Nowadays, you’re lucky if the person keeps from posting your text message breakup conversation to Instagram. Hashtag, disrespect.

Once single, the entire process starts again, often times people jumping into new situations before healed or ready. What use to be called a rebound has become a mess of people who won’t necessarily be clear about their intentions, to themselves or the person they are using as a distraction. That’s not to say anyone is ever completely healed after suffering heartbreak, but its best to try and carry as little baggage into your next relationship as possible, instead of moving in the entirety of your luggage.

And then we’re back to spending countless hours updating our OkStupid accounts, sifting through Missed Connections and fielding more and more rejection. No one likes to hear it, but actively seeking a relationship is often times the number one reason you’re not in one. Trying to force a connection is the quickest way to land yourself in a forced relationship. That’s not to say you shouldn’t continue to put yourself out there, but instead of constantly seeking, put that insatiable search on the back burner. Stop trying to make dating happen. I promise, doing you will make dying alone will seem far less realistic.

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