All The Things No One Tells You About Dating As An Adult

7 min readDec 15, 2020


When we are young, we often don’t see many examples of single people in their 30s, 40s, and beyond who are actively trying to date. We are taught that marriage usually happens sometime in your 20s, maybe in your early 30s if you are really taking things slow. Sometimes adults in our lives get divorced, but they almost always remarry. There is the occasional family friend or aunt who stays perpetually single but as a child, you don’t really think about what that means, because no one really talks to young people about dating and relationships. No one talks about how hard all relationships are, which ends up doing us all a disservice as we grow up. No one tells you that sometimes in your 20s, 30s, or even later, a relationship will suddenly (or maybe not so suddenly) end, and you will have to just start everything over. But this time, everyone you are trying to date brings baggage and life experience to dating that no one has in our younger, more naïve and fun early 20s. There are so many things that no one prepares you for when it comes to dating as an “actual adult.”

Nothing can prepare you for how bad at conversation the majority of people are.

No one explains that moving on from past relationships is not as simple as just “getting over it,” as society has led us to believe. You will eventually look back on things with such mixed feelings, and in time you might even come to appreciate the ambivalence.

No one warns you that people will weaponize your best qualities and your biggest accomplishments against you. No one tells you that people will find ways to take the things that you love most about yourself and use them as reasons not to date you. No one prepares you for the amount of time you will spend wondering if you are just “too much” for some, and “not enough” for others.

Society’s love of fairytale romances tells us that as soon as we have an amazing first date, we will end up with that person forever. No one tells you that sometimes, your best first date will be with someone you never have a second date with.

No one explains that you will learn new things, either about the world or about yourself, from almost every new person you meet. And that sometimes, out of the blue, something will remind you of someone you haven’t thought about in days or weeks or months and you will be surprised to notice that you feel a little sad. And then, you will feel a little silly for still thinking about someone that you are quite sure never thinks about you.

No one warns you that sometimes, you will be the only person you know who is still single. It will feel like everyone finds people easier than you do. You will spend a lot of time wondering what is wrong with you and considering whether this is karma for the mistakes you made in previous relationships, or whether you did horrible things in a past life. No one tells you how good you will get at holding two conflicting feelings in your heart at once — how you can be genuinely happy for others, yet sad for yourself. No one explains how guilty you will feel when someone you know has a relationship end and you will feel all the sympathy and empathy for them and you will want nothing more than for your friend to stop hurting, but suddenly and surprisingly a small voice will pop up in the back of your head that says “At least I’m not the only one anymore.” No one prepares you for how terrible that will make you feel, and you will hopefully be able to chase that thought away as quickly as it came.

No one warns you that sometimes the people who engage your mind the most can destroy it the fastest.

No one explains how many people you will meet that you just know that if things were just a little different — another time, another place, different career situations, if they more actively engaged in therapy or were further along in their therapy journey — they would be an amazing match for you. No one prepares you for how much time you will spend thinking about these people, long after your time with them has ended.

No one lets you know that there are many positives to being single. Doing whatever you want, whenever you want. Being able to focus on cultivating deep friendships, spending time with your own family and not having to divide your limited free time with the other person’s family, being able to make any career change or move you want to make and not having to ask anyone but yourself, traveling with people who fit your personal travel style or even traveling alone and not having to worry about accommodating a significant other. No one tells you how much you will come to enjoy and appreciate these positive aspects of singlehood. But on the flip side, no one warns you how expensive it is to be single either.

No one explains that after a certain amount of time, you will start to feel like you are better off alone. And you will really, truly, believe it most of the time. You will be able to create a life you love, and it will be yours and yours alone. And that will make you feel powerful and in control. Sometimes, you will be able to ride that wave for the rest of your life. Other times, a massive global catastrophe will occur that will change your whole viewpoint on being single and will add a heaviness to dating and to everything else. No one warns you about those damn global catastrophes.

No one prepares you for the fact that once you have come to genuinely love being alone, you will start to view everyone you meet through the lens of “Is this worth giving up parts of the life I have created for myself?” That is an impossible standard for anyone, but particularly a stranger, to meet. No one advises you on how to strike a balance between having standards and being realistic.

No one talks about the fact that even when you meet someone great, it takes a long time for all those years of walls and defenses to come down. No one tells you that you will still, even when you are with someone good, spend a lot of time wondering what is wrong with you because you at times can’t even fully appreciate it. No one prepares you for the fact that you have spent so many years wondering why more people are not in therapy, and as it turns out you are not exempt from the need for therapy.

No one prepares you for how awful it feels when you meet a great person that for whatever reason, you just don’t have a romantic interest in, as much as you wish you did. And no one prepares for how awful it feels when that happens in reverse.

There are so many things no one tells you. So, let me be the one to tell you: everything I wrote above, the good and the bad, is happening to someone right now even if it isn’t happening to you. There are so many more feelings and situations I couldn’t possibly summarize here that are also happening. Sometimes being single feels amazing, sometimes it feels terrible, and sometimes it doesn’t feel like anything — it just is. But let me also be the one to tell you this: if you can keep your mind and heart open, if you can view every new person you meet as a learning experience or as a brief moment in time instead of expecting everything good to last forever, you might find that the good can often outweigh the bad. If you can look back on people and situations as fun things that you leaned into because they worked at that time, you can eventually learn to view them in a positive light instead of viewing them as things that ended prematurely or unfairly. If you can think of someone in terms of what they taught you and not what they did to you, you might enjoy the process more and you might grow into a better version of yourself. And, if you are really lucky, you will make new friends along the way. Whether you meet friends on twitter, join meet-up groups, or meet people through new hobbies (that you have time for, because you are single), your social circle can expand in ways you never would have imagined. No one tells you that one day you will look around you and realize how many important people in your life wouldn’t exist if it weren’t for your time being single. No one explains how much more time and effort you are able to put into friendships when you are single, and how these friendships will teach you to love in newer and deeper ways, and these skills will in turn help you in the dating world. No one else will tell you, so I will: if you keep an open mind, if you make the most of your life in any way you can, you will be okay. You will still have hard days, sad days, and lonely days. You will still wonder what’s wrong with you sometimes. But you will be okay. And if 2020 has taught us anything, it’s that okay is actually pretty damn great.




Lover of dogs, food, coffee, bourbon, and exploring new places.