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Jamie Rea

Say a guy goes five years without a relationship, that’s five years without ever committing to one person, or having to control or refrain from giving into temptation and attraction.


What Happens When You Stay Single For Too Long

Comedian Bill Burr has a famous line in one of his stand-ups; “There’s a critical point when you’ve stayed single for too long, that your brain switches from ‘No, don’t say that’ to ‘Eh, fuck it. Say it, see what happens.”

What he was saying is that when you go a long time without being in a relationship, you can take a few more chances. Why? Well, you’ve been alone before, and have survived. Fuck, you may have even flourished. Thus being in a relationship isn’t the be-all-to-end-all. You know that life doesn’t end if this relationship ends. So why not push the boundaries in your relationship and see what you can get away with? If it doesn’t work out, you’ll survive, you may even flourish all over again.

So this brings about the obvious questions…

Are you more likely to sabotage a relationship because you simply just don’t care?

You see this is the very problem you run into when you’re been a single for too long. You tend to kind of not care about anyone else as much as you should. Even if you meet a woman who you really like, even love, you may run the risk of jeopardizing your relationship when you carry over the habits you’ve been doing for the past however many years as a single guy. The hard truth is that you need to change certain things about your behaviour when you’re in a committed relationship with someone. In theory it shouldn’t be difficult to change for this person because you love them, or at least like them, and want to do everything you can to make it work. But it’s often easier said than done. It’s at least something you need to be cognitive of so you don’t push away this person you care about with your “I don’t give a fuck about anything” attitude.

Does the longer you stay single mean your chances of finding the right relationship will continue to decrease?

It’s the obvious worry to someone that’s been single for a long time that they’re going to run out of time — all the catches are going to be snatched up, they’re going to become out of date, old, expired, and not in prime position to meet someone of quality, thus their standards are going to be forced to deteriorate over time, just as they’ve themselves been deteriorating. Their need to find the absolute perfect person has been the primary contributing factor to their permanent single status, leading them to go on multiple years without an exclusive relationship. So sure you’ve been single a long time, but you have to trust that you’ve stayed single because you know what you want in a romantic partner and aren’t willing to settle for anything less than you think you deserve, just as long as you aren’t picky to the point that you expect everyone you meet to be perfect.

Once you stop using that relationship muscle, do you lose it altogether?

Just as someone who goes months and months without sex may be worry their genitals will become dried up and not functional, someone who goes for so many years without an actual relationship may worry their capacity to be happy and functional in a committed relationship may leave them as well. While it’s definitely going to be a hell of a transition going from being VERY single to all of a sudden being in a relationship, but you have to trust that it will be easy when you find someone you care about enough. Also, the fact you’ve been single for so long and have such a strong sense of self might make you a better partner in a relationship. It may be of your benefit to find someone of a similar independent personality type in a similar position to you (been a while without a relationship) who can allow for a relationship dynamic that enables both of you to still keep your independent lives, while making a concerted effort to make time for each other and meet in the middle.

So when this guy eventually does find his next relationship, what are some of his behavioural tendencies from when he was single that may carry over and put a strain on his new relationship?

For starters…

He may flirt more than is considered appropriate for a taken man. Say a guy goes five years without a relationship, that’s five years without ever committing to one person, or having to control or refrain from giving into temptation and attraction. A single man sees a hot girl; he does everything in his power to have sex with that hot girl. A guy in a relationship sees a hot girl, he probably wants to have sex with that hot girl but he doesn’t because there is this other human who would be completely and utterly destroyed if he did. The guy who hasn’t be in a relationship for five years probably won’t cheat, but he may have a hard time controlling his attraction to a manner that is deemed appropriate for a committed man. When you’re single for so long, you flirt freely, without any repercussions for your behaviour, but a guy in a relationship is always under a microscope in terms of how he talks to the opposite sex. It’s not an easy thing for a guy who’s been out of the game for that long to re-learn what is considered appropriate and what is considered to be crossing the line. Even in terms of what should be considered straightforward inappropriate behaviour like texting with other women, messaging them on social media, or taking flirting in person too far, sometimes are not easy habits for these guys to kick. There’s nothing wrong with a certain level of flirting in a relationship, in fact it’s actually healthy in the right amount, but you have to be aware of the message you’re sending to other girls, particularly to those who don’t know you have a girlfriend and might be led on.


Guys who go so long without relationships often have grown to be selfish. It’s the little things that you learn from being in a relationship: making plans and decisions together, deciding what restaurant to eat at, sharing your bed, remembering to return their messages and call them before you go to bed, and just having to consider someone else’s stance and opinion on everything you do. A guy who is used to being single does his favourite things all the time, he never has to make compromises or actually think about how his actions will affect another person. He’s free to party when he wants, drink to excess and make a fool of himself because the only person he has to embarrass is himself, turn his phone off and disappear from the world when he’s hungover because he doesn’t have someone constantly wanting to know his whereabouts, and he can sleep with however many women he wants and doesn’t have to worry about his slutiness affecting anything but his own moral conscious. Relationships teach us to co-exist with someone else, to learn how to work together with someone and create a partnership, to understand that the world doesn’t revolve around us, and sometimes we have to do our second favourite thing so the person we care about can do their favourite thing.

Being single and being in a relationship are different gears. For a guy who hasn’t shifted into the relationship gear for a while, it’s going to potentially be a rocky transition. Before he just lived his life for himself, and now he’s learning, again, what it’s like to share your life with another human being. That’s the struggle, and the beauty of it. Relationships are extremely difficult because we have to work our way through the world, knowing that someone cares so deeply about everything we do, that our pain becomes theirs, that our happiness is their happiness, and someone who’s heart could be shattered if we betray them. That’s a lot of responsibility for someone, especially someone who hasn’t had to deal with that responsibility in quite some time.

This is why engaging in relationships are such valuable experiences, even if they end up failing. We learn about how to care about someone else, how to put the happiness and well-being of someone else ahead of ourselves, how to make decisions and compromise with a partner, and how our decisions have the ability to impact other people on extreme emotional levels. Relationships teach us to become more emotionally responsible, better communicators, and better able to get along with other people. Most importantly, we learn and discover more about ourselves. The “relationship version” of yourself is going to be much different than your “single version”. This is because you live with more heightened emotions, you’re more vulnerable and sensitive because someone else makes up a big part of your happiness or your despair. You can figure out if you’re a jealous person, what type of personality types suit yours on a romantic level, and what role you like to take in a relationship — is it more of a submissive position to your partner? Do you like to be the one to take control and make the decisions? Or do you operate best on an even playing field?

So for the guy who is treading relationship waters for the first time in a while, sure it might not be easy, you might fall on your face, you may feel uncomfortable, and you surely will make mistakes. But soon you will remember the beauty of being in a relationship, this person you care about will help you to think outside of yourself and to care about things that are greater than your own little tiny, first-world problems. And once again you’ll be reminded of the simplest of truths: your happiest moments are shared and you can’t experience true happiness unless you have the ability to care about someone else more than you care about yourself.

Bill Burr was right, when you haven’t been in a relationship for a long time you’re willing to take more chances because you aren’t dependent on relationships for happiness. But what he seemed to leave out — while you may be willing to take risks to test your partner’s patience and “coolness”. It’s all just to cover up the fact you’re scared and your instincts are telling you to run in the opposite direction as fast as possible because then you can’t be hurt by this person who now has partial dictatorship over your happiness. The greatest risk of all is…staying…and giving in to the fact you’re actually starting to care about someone: someone who now has the ability to destroy you.

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