Settle Down or Sleep Around: The Confusing Mixed Messages We Receive About The Purpose of Our 20s

Settle Down or Sleep Around: The Confusing Mixed Messages We Receive About The Purpose of Our 20s
In one corner, your parents, peers, and tradition; in the other, pop culture and a macho society. It's a bloody battle.
Settle Down or Sleep Around: The Confusing Mixed Messages We Receive About The Purpose of Our 20s

I’m 25 years old, smackbang in the middle of my 20s. According to pop culture media I’m supposed to be living life to the fullest, going to parties, loitering in bars, and sleeping with anyone and everyone who I can persuade to take their clothes off. Then again, it also means I’m supposed to be solidifying my career, putting away savings, and finding that special someone I can settle down with before I hit the big 3-0.

There’s a fundamental inconsistency here, an incompatibility that runs right through the generation currently going through their 20s (millennials, not that I’m enamored with the term). On the one hand our adolescence is ever expanding, the old comic conceit of the ‘manchild’ becoming less punchline and more par for the course. On the other hand, there’s still pressure, partly from older generations but just as much from ourselves, to hit the big milestones of life, to buy a house, get married, settle down with kids – all with the vague sense that if you’re not at least part of the way there by 30 you must be doing something wrong.

Nowhere is this more true than when it comes to romantic relationships. Enter a steady, long-term relationship – especially in your early 20s – and you face the common cultural notion that you’re wasting your best years, missing out on the chance to sow your wild oats, meet new people, and learn who you really are. But spend too long single, too many evenings aimlessly swiping through Tinder or wandering through bars, and the opposite worry creeps in: that you’ve left it too late, as everyone around you seems to be settling down, marrying, and moving onto the next chapter in life. Leaving you behind all by yourself.

So, what’s a confused 20-something man to do then? Sleep around or settle down?

Settling Down: “Everybody Else is Doing It”

It may at first sound daft to suggest that anyone is going into long-term relationships out of little more than peer pressure, but there’s something to be said for it. Especially entering the second half of one's 20s, it can be all too easy to look around and worry that everyone else seems to be marrying off and settling down. This is never more true than when entering the summer, as your calendar begins to fill up with wedding invites – often for both this year and the next – and everyone starts to look around and wonder who’s going to be next. Throw in the fact that for many couples marriage is the immediate precursor to having kids, and it’s all too easy to get the sense that the singletons among us are falling rapidly behind.

It’s an understandable anxiety, and one tapped often enough by pop culture. No one wants to lag behind their peers, in careers or in relationships, and I suspect most of us have felt that niggling fear that we’ll be the last one left single, the only one among our friends still clinging onto our extended adolescence while the rest of them get on with being adults, whatever that means.

This is, of course, also a very silly reason to do anything, least of all enter a lifelong, committed romantic relationship. Sure, plenty of your friends may be wedding one another, but I’ll wager it’s not all of them – and it won’t be for a while yet, if ever.

This also comes with a huge logical fallacy. Since you’re a Primer reader I already know you’re more introspective, more disciplined, and desire more for yourself than most of the population. By assuming there’s something wrong with you because you’re single, you’re suggesting that everyone you know who has gotten married has the same high standards for:

  • How satisfied, attracted to, and in love they are with their partner
  • Having the strength to walk away from a comfortable relationship if it isn’t right (most can’t)
  • How compatible the communication and values are, emotionally and sexually (most settle)
  • Having incredibly high levels of respect for each other, to challenge and inspire each other, and to support each other even when you disagree

When you look at it this way, you may know one couple, if any, that has such a motivating relationship. By demanding more of yourself and your relationships you are committing to a life full of self-respect and confidence.

This can be seen as a parallel to the famous Dunning-Kruger Effect, a cognitive bias where intelligent and skilled people underestimate their own abilities and assume their peers are as or more competent; and relatively unskilled persons mistakenly rank their ability to be much higher than it really is. Read: You’re likely an amazing partner – that doesn’t mean your married friends are. Because of your higher level of respect for your partners, yourself, and your relationships, you assume everyone else is as emotionally capable to do the same. They’re not.

Settle Down or Sleep Around?

Sleeping Around: “Your 20s Are the Best Time for It, Right?”

A seemingly obvious point in favor of avoiding strong ties: sex is fun, and by extension sex with lots of different people should be even more fun. There’s a pretty widespread, natural urge for variety when it comes to sexual partners, and your 20s are a great time to scratch that itch – you’re young, you’re (relatively) carefree, and you’ve probably got the most free time you’re going to have until you hit retirement. Well, if you ever get to retire – our generation is looking a little shaky in that regard.

Beyond the pure enjoyment of it all, it’s also incredibly educational. You’ll learn plenty about sex from trying it with different partners, from what you like to what they tend to, and that’ll be useful knowledge to have by the time you do find yourself in a committed relationship for good. Both for having a strong and healthy sexual relationship with your spouse, but also for eschewing fear-of-missing-out anxieties that are common among men once they’ve been in a long term relationship that has naturally settled down.

On the other hand, the single life isn’t always all it’s cracked up to be. No matter how many scaremongering Vanity Fair articles you read, Tinder hasn’t exactly turned us into a generation hooked on casual sex – in fact there’s some evidence that we’re having even less of it than previous generations.

In a committed relationship you can have a pretty regular sex life as long as you’re not going through any particular problems. Being single might offer more varied sex, but probably not more of it full stop. There are more nights in on Netflix than nights out on Tinder.

A lot of the argument runs that you should use your 20s as a time to date lots of different people simply because there’s never going to be a better time for it. You’re young, your likely partners are young, and, so it goes, you’re all as good looking as you’re ever going to get. You should have less baggage, less risk of serious exes, divorces, or kids to worry about. You’re also more likely to have a social life that already revolves around going out and drinking (ir)responsibly, which suits being a singleton pretty well.

I get the argument – and it’s part of what made me pause for thought during my last committed relationship – but more and more I’m questioning how much it holds water. The rise of online and app dating has helped break down some of the barriers for dating – as long as you have Tinder or OKCupid, you can meet new people without having to commit every Friday night to bar crawls and overpriced clubs.

There are advantages to dating beyond your 20s too. You (and your dates) might well have a bit more disposable income, which takes some of the financial bite out of heading out to a new bar for drinks every few days. Plus, if you’ll pardon my French, you’re both more likely to have your shit together: to know what you want, to know how to be up-front about it, and hopefully to know how to handle all of the inevitable rejection that comes along with dating. You’ll hopefully have gotten out of bad habits like ghosting or standing people up. In short, you’ll basically be more of an adult, and so will they, and everyone will probably have a better time for it.

Settling Down: “Relationship Practice”

Relationships are hard. We all know that. I mean, honestly that’s the whole basis on which I get paid to write this stuff. None of us know exactly what we’re doing, we often get it wrong, and we’re all struck with a dumb sort of awe every time we come across one of those couples who just seem to somehow have it all figured out.

Most of the time when we set ourselves to any especially challenging task we accept that it’s probably going to take some practice to get good at it. Whether it’s learning to drive a car, play a musical instrument, or master a sport, we know we’ll have to put in some legwork getting it wrong before we start getting it right. So why should relationships be any different?

This is, in a roundabout sort of a way, an argument for aiming to establish serious relationships while you’re young. Serial dating might improve your small talk, your flirting, and, if you’re lucky, your sexual knowledge, but it’s not going to help you learn how to deal with major arguments, communication breakdowns, or breaches of trust. You’ve got to invest in a relationship, to make yourself vulnerable, to experience those issues – and thus learn how to deal with them, improving this and all your future relationships.

Think about it this way: do you really want to spend years avoiding commitments and having fun, then finally find the person you want to spend the rest of your life with and screw it up because you’ve got rubbish communication skills and don’t know how to move past your first serious argument? The relationship issues you face in your 20s may not always be the same as the ones you’ll come across later on in life, but they’ll all help you prepare, make you a better boyfriend or husband, and hopefully stop you from losing your dream girl or guy whenever you do find them.

Sleeping Around: “You’re Going to Want to, Might Regret It”

Perhaps the most persuasive argument in favor of not tying yourself down – at least to those people already in serious relationships and wondering if they should be – is the thought that you might regret not doing it later on.

This worry has two halves. The first is that you’ll regret not having done it in your 20s because it’ll never be quite the same later on. And sure, you’re less likely to get to date 20-somethings again later in life, but otherwise we’ve already seen that the argument doesn’t quite keep up.

The second fear is that in fact you’ll end up with your current partner for the rest of your life, and you’ll never get the chance to be a bit more sexually free again. This is a concern that gripped me for a good while, but looking back it seems distinctly like nonsense. First up, if you do end up with this one person for life, then great! That hopefully means you genuinely, actually love each other, and get the sort of lifelong relationship plenty of people dream about. That is not something to fear.

But second, beyond the complications of kids, you’re not going to be more restricted than you are now. You might be thinking that you’ll never get to sleep around because you’ll always be in a relationship, but that’s clearly exactly true right now, and you’re still thinking about it. You’ll always have the options of ending things to go try your luck with other people, so there’s really no rush about it. If your relationship is in trouble for other reasons and you’re thinking about ending it regardless, that’s a whole different thing. But don’t end a perfectly good relationship just out of fear that you’re missing out on dating some hot young things – they’re not going anywhere.

What to Do?

If you’ve read this far, you may be feeling frustrated right now – I haven’t really answered very much of anything. Should you sleep around? Yeah, maybe – there are some pretty good reasons. Should you settle down? There are plenty of strong reasons for that too.

What’s important isn’t what you do, but why. There are good reasons for either approach – but there are bad reasons too. Which feels true to you right now?

From the Editor: Andrew's Experience

In a matter of weeks I’ll be 32 years old. An age I would have considered to be a “man” at every other period in my life. I am single. But I wasn’t always. Starting at age 20 I was in a relationship for 9 years with someone I loved more than anyone else I ever had and planned on marrying.

But we never got married. We both agreed we wanted to, but it was never the right time, whether dealing with post-college financial realities, significant health issues, building Primer while working full time at a long-hour job – it was always something that we were going to do later.

We wanted to be married but we weren’t ready to get married.

I’m not sure why that was true for her, but for me, in retrospect, there was always this nagging voice in the back of my mind that would pop up every so often asking if she and the relationship were the most compatible for me. Resulting in fears that my future Mid-life-crisis Self would be bogged down in an unsolvable existential disaster because I spent my 20s in a loving but comfortable relationship instead of overcoming my personal limitations, meeting new people, and learning who I really was.

Ultimately she was the one with the strength to end it. I would not trade the years I spent in a relationship for years of young dating. I'm a significantly better person and significantly better partner for having been in that relationship, but sometimes the things that get us into a relationship change or are no longer true, and that's when they end. For me, that means I've matured into a version of myself that is closer to what I've wanted all my life and learned more about myself and what I'm looking for. In the end, this was a win-win situation; we got to experience all the amazing parts of our relationship together, and we both got to continue growing individually when that was no longer possible as a couple.

For you, it may mean marrying your college sweetheart. Or staying single until your 40. Or dating someone to see how things go and making the decision later. There are a lot of ways you can tackle it and come out stronger, more mature, and happy. The “right” way is the way that feels most true to yourself, regardless of what your partner, peers, or parents push on you.

The most important thing you'll ever do in your life is learn which voice in your head is your intuition, and which one is fear and doubt. If your relationship doesn't feel right, even if it's good, you should listen to that. Maybe that means you or both of you together need to do therapy to untangle it. Maybe it means the relationship has run its course and it's time to move to the next chapter in your life.

If you're single and happy, whether you're sleeping around or not, then that's all that matters. Maybe, for you, this is exactly the right thing to be doing. And if some day that becomes not true, you can make that realization and seek out a committed partner.

And if you're single and frustrated, remember it's not because every other guy is more attractive and a better option. Those guys could be dealing with their own struggles or may have lower standards than you in what you need in a relationship to be happy. The reality is you could go out tonight and meet someone and have a lifelong relationship with them. That doesn't mean it'll be fulfilling in the way you need it to be. So take heart: You're single because you hold yourself and your relationships to a higher standard than most. As long as you can comfortably say you're working on being the best version of yourself everyday, there's nothing to fear. You will meet your optimal partner in due time. (And you'll likely be grateful for this time alone as indispensable for your growth as a person.)

So should you settle down or sleep around? I've done both and am incredibly thankful for having both experiences. You have to decide which is best for you, where you are now.

This is one of the toughest things for guys, share your story in the comments.

A London-dwelling philosophy graduate with a penchant for films, gaming, and technology, with the occasional bit of tennis thrown in there.

  • Loscv29

    At 31…. I just NOW finally started to cement what I want out of my romantic relationships. I think ones 20s should be all about figuring who you are and how you work. Its important that you be good to yourself and not take on anything toxic. Relationships should help you grow as a person.

  • mikeypikey

    Thank you guys for making my day !!

  • Jamie

    Excellent piece, especially the editor’s addendum. Keep up the good work.

  • Yingerman

    Thank you for sharing your story, Dominic. Like you were, I’m in a loving but comfortable relationship and I’ve been going through a lot of these thoughts myself.

    I’m curious, what was it like ending a relationship with someone you’ve spent 9 years with? It sounds like you left things on good terms — was it possible to stay friends?

  • Ross

    Well said, sir. Very well said. Invictus poem comes to mind in reading the final few paragraphs.

  • jbird669

    This is a great article. I have a unique perspective on this. I am 37 and I was married in my mid 20s. It didn’t work out. I can say, with hindsight, that I wasn’t ready to be married, emotional!y or financially. Now, is anyone really ready with the latter? But I think you need to be emotionally ready, which comes from dating. Now, I am able to date (and “date”) a variety of women. IF I get married again, I am better prepared.

    Lastly, this site, and others like it, are invaluable. I didn’t have these in my 20s. Don’t take it for granted.

  • Skinnytie

    As someone who just turned 25 two weeks ago, works a professional job, and goes on multiple app-catalyzed dates every week this hit home. The thing i think I’ve learned is the ability to shut doors, In college and after it was unheard of to say no to a woman, if she was cute and willing why would you, she could flake, dis respect and repulse me but her wanting me even only sometimes was enough to put up with all the bad, but you realize the old cliche of “plenty of fish in the sea” is more true than ever and you shouldn’t waste your time being disrespected simply because she is pretty and giving you attention. If you’re working on yourself and hold yourself to a higher standard its okay to cut ties with someone because they aren’t treating you with respect, there will always be more pretty, interesting women/men. DON’T SETTLE out of fear that this may be as good as it gets for you.

  • Lindsay Schramm

    Wonderfully written.

    Sometime I cherish about my relationship with my boyfriend (we are 31 and 30) is that we spent our twenties not only both in a couple medium-length relationships (2 or three years), but also sowing all of those wild oats. Now, not only have we learned what works and doesn’t work for us in relationships, we also know what works for us sexually, and don’t have a bucket list of dirty things we never got out of our system. Well, except for the ones we want to get done together!

    I’m very happy I waited until 30 before “the one”.

  • Rt1583

    A quote from a good book I’ve recently started reading that, I think, fits with the duality of the topic at hand.

    “The past reflects eternally between two mirrors -the bright mirror of words and deeds, and the dark one, full of things we didn’t do or say.”

    Gregory David Roberts, Shantaram

  • Nicholas E.

    23 and just broke up with the person I thought I’d marry. Moving to an incredibly small rural community for work (she didn’t want to move), and I’m assuming I won’t be dating there. No romance for a couple of years, maybe. I might be in my mid-late 20s again before I live in a place with a dating scene of any kind. Not sure exactly where to move later, but I’m not thrilled about the situation. I look forward to finding my mid-20s to “find myself” a bit, at least.

    • Erick

      This kinds of hit me a little. I have one more year (5th year) of college and I’m doing a really good internship that will likely turn into a job. I don’t know if my significant other is going to be willing to move to for me to start my career and I also don’t know that I’m willing to stay while she finishes grad school. I’m also terrified of thinking of a life without her. I guess you could say I’m stuck between a rock and a hard place. I hope you find even the smallest of a dating scene wherever it is that you are.

  • http://differenthunger.com Matt Kohn

    Awesome post! We must not get pressured if others are already marrying and having kids. You’re the only one who knows when you’re ready. There’s joy in being single. As a wise man once said, if you can’t be happy being single, you can’t be happy being married. 🙂

    -Matt Kohn

  • Jackie

    So I just turned 32 and my female perspective is that I did my life backwards. I got married and had kids young 21. I Went to college and started by nursing career. 10 years in, I’ve never been so unhappy because I’ve been in a toxic relationship and felt that settling down was what everyone did and that was my expectation. So now I’m newly separated and absolutely love my life. I’m not sleeping around… But not walking on eggshells is so freeing. I should have spent my younger years learning who I was, but wouldn’t trade my babies for the world.

  • And That Is The Serious Truth

    It is very hard these days to turn a Whore into a housewife.