Dating Dilemma: Reasons to Be Single, but…

There’s a horrible dilemma in relationships.

We want to be single in a relationship or we want to be partnered with independence.

When we are in one, we so often long for the freedom of independence and we we aren’t we seek companionship. There are a lot of reasons to be single, but there are also a lot of counter arguments to being in a relationship.

The big question becomes: how do we find happiness amidst this dilemma?

How do we find a relationship that doesn’t leave us desiring independence? How do we find happiness in independence that doesn’t cause us to settle into relationships as a result of lowering our standards from fear of lonesomeness?

I’ll try and answer that question, but first let’s examine this paradox in detail. Here are 10 reasons to remain single with their “buts”.

Come and Go As You Please

Here’s the big one, right? We answer to no one but ourselves and if we want to stay out until 3am splipping dollar bills into g-strings on a Tuesday, that’s our perogative. I wouldn’t recommend it if you have to wake up for work, but no one is going to be blasting your desire to leave the house whenever you want, change up plans, and live a life entirely on your terms.


As endearing as sponteniety can be and as liberating as answering to no one feels, there’s a certain emptiness in that life that compels us to partnership. Yes, we can come and go as we please, but the craziness of being on the go becomes a distraction to what happens when we find ourselves riding in a car in solitude, making dinner in our kitchen alone, and wishing we had someone to share our adventure with.

Be As Frugal or Lavish As You Want

One of the major challenges of all relationships when they’ve hit a particular point of dependency, is the struggle with whether and how to mingle finances. Regardless, differences in financial responsibility and expectations of lifestyles can rock even the most loving relationships. When you’re single, it is your life style, your money, and your financial decisions.


Rent and utilities are fucking expensive. Every little bit helps, so finding that person to not just Netflix and chill with, but actually share the Netflix account with is pretty sweet. Finding the person you love enough to invite them to live with you is awesome, because you now have a roommate you get to joke around with, talk to, and sleep with that may help pay the bills.

Have No Strings Attached Sex

If you just want to increase your body count, the single life is where it’s at. Can’t be a cheater if you just perpetually don’t commit to anyone. And variety is cool and I think as guys we would be lying to ourselves if we didn’t suggest there is always this urge and curiousity in smashing different women without having to meet obligations of a relationship.


There’s also a sense of comfort in having sex with someone we love and spend our time with. Sex in relationships might not have all the excitement of the unknowns or a new lay, but she knows what makes you tick, how you like certain moves, your kinks and your favorite positions. That’s valuable to a sex life that doesn’t exist just randomly jumping from person to person.

Buy Yourself Presents

Holiday season brings a newfound enjoyment to relationships, but in that joy is often a surmounting pressure to find the right gift. The single life dismisses that pressure, because when you’re single you only have to worry about buying yourself a gift…and maybe your mom, but she won’t care what you buy!


As much pressure as there is, when you finally find that right gift and her eyes light up, that’s a very rewarding feeling! Not to mention, its pretty nice to be surprised yourself!

Double Tap Those Thot Poses

Instagram is full of eye candy! Maybe it’s a celebrity, maybe it’s the girl next door, or an ex – you can like that post without any consequences. If you have a girlfriend and she sees you put a heart on your friend Claire showing some sideboob, you’re getting to receive some major shade.


Having a girlfriend brings a whole new dynamic to your own social network life. Now you’re not just the creepy guy that hearts every girl’s photos.

Travel On Your Terms

While slightly related to both being “frugal or lavish” and “coming and going as you please”, the freedom of travelling to places you desire instead of compromising is pretty cool. If you love the mountains and she loves the beach, this is a problem. If you want to go to Australia and she wants to see Las Vegas, this is a problem


Traveling alone, as adventurous as it can be, is also pretty boring. Sure you can find some random peeps at a hostel, mingle at a local pub, or converse with the guy next to you on a plane.


When you’re 2 hours in on a 8 hour hike, there are times despite the serenity of nature, that you just wish you had companionship. I drove 15 hours to Colorado for a weekend getaway, and about 3 hours in I was considering turning back. I love meeting new people, but at the same time, every trip I took consisted of meeting new people to a point I craved comversation with familiarity.

How do you navigate this dilemma?

How do you find happiness when being single causes you to crave companionship and being in a relationship causes you to desire independence?

I’m not sure I have the perfect answer for that, as I think our brains will always entice us to what we don’t have. Part of our happiness comes from just accepting that. Sometimes we just have to accept that no matter how often we swap lawns, grass will always appear greener elsewhere.

Finding happiness while being single requires us to seek out distractions that keep us busy and motivated. Some people are introverted and love their personal space, but I think its important to avoid secluding ourselves into a cycle of depression where our inability to put ourselves out there only further hurts us, making it yet more difficult.

Finding happiness in relationships that don’t leave us wanting something else I believe requires us to be patient and seek out that “fuck yeah” person. I think relationships require committment with healthy amounts of independence. You have to wait for the girl that you want to respect and love, not the one you can respect and love.

Wait for the girl that shares your sense of adventure and that’s so beautiful in your eyes you could never imagine life without her. That’s how you avoid unhappiness in the paradox.

So many people settle into “meh” relationships. The sex is “meh”, polar opposites of personality, interests that don’t align, or some other aspect of the relationship that just feels like we’re compromising. Compromising on our standards is not what compromising in a relationship is about.

Our friends will tell us we’re being too picky while they turn around and complain about the relationship they’re in, and over time as our desire for a relationship increases, our demands for what we want from one decreases. Those initial desires never really go away, though, so when someone new comes along, we’re feeling so “meh” about the relationship we’re in we consider the idea that this new thing before us could be what we really wanted all along.

Defeating the paradox requires us to find purpose in our independence and to not accept “meh” relationships.

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Hi, I spewed out all the shit you just read! I like long walks on the beach (but I'm mostly surrounded by cornfields), challenging the status quo of the dating scene, fucking all the rules of dating and encouraging men to live their best life. When I'm not trying to keep the lights on around here and raise two little girls, you can find me drinking and partying - you know the key Wallstreet success...ballin'.

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