In today’s video, I talk about 5 things I wish I knew about relationships when I was 20 years old. (**Younger retroactive jealousy sufferers please take note!)

Read on or watch below to know about my top-5 relationship mistakes I made in my twenties.

Zachary Stockill: As I was reflecting recently on my YouTube videos and on my channel, I realized that I spent a lot of time talking about all my accomplishments and all the things that I have that I get right, basically, in terms of retroactive jealousy in terms of my coaching practice and all the rest. So I thought it was probably time for me to share a video talking about some more of my relationship mistakes, sharing some more of the things that I got wrong

Over the years, one of the most fun parts of my job is working with younger people. And when I say younger people, I’m mostly talking about young men and women in their 20s.

But one of the things that I really enjoy about working with younger men and women is hopefully I can help them avoid a lot of the same dumb things, some of the same relationship mistakes that I made when I was their age. And I was thinking recently: if I could sit down with 20-year-old Zach, have a beer with him and share a few pieces of wisdom, and share some things about what not to do in terms of his relationship life, what would I tell him?

Today, I want to share five things that I wish I knew about relationships when I was 20. The first thing…

I would tell my 20-year-old self: you’ve got time. Slow things down. There is no rush in terms of things like moving in together, and getting very, very seriously involved.

… and combining your finances and doing all these kinds of crazy things that I did when I was a 20-year-old man. I think when we’re young, and we fall madly in love, there’s this temptation to speed the process up, you know, become really emotionally invested very, very quickly, maybe move in together very quickly, maybe get engaged really quickly, maybe start commingling finances and spending every waking moment together and rushing up the courtship process. And there’s no reason to do this. 

In fact, there’s a lot of very compelling evidence that suggests actually taking your time and relationships is actually the best way to approach relationships. And I wish I did this myself back when I was 20. 

You know, when I was around that age, I fell madly in love with a wonderful woman. And we moved in together way too quickly. I basically became a married man overnight, because when you live with someone that’s pretty close to being married to that person, even if you’re not married on paper. 

Now, I don’t have regrets, per se, because obviously living with someone taught me a lot about relationships and women and all the rest. I don’t regret it per se. But if I had a time machine, and I could have a word with my 20-year-old self, I would probably tell him to slow things down. There’s no rush with these things. You’re 20 years old; you’ve got lots and lots of time. 

The second piece of advice I would give is:

Don’t make your woman your world.

Or, if you’re a woman watching this, or if you’re a gay man watching this, you get my idea: swap whatever gender you want, don’t make your partner your world. 

Another mistake I made when I was in my early 20s is to a considerable extent, I made my woman my world. I let a lot of my friendships kind of slip by the wayside. I let some of my hobbies and interests kind of slip by the wayside. I didn’t have real goals in terms of you know, short term personal development goals are short term career goals, or educational goals are all these things because I was so madly in love. I was so consumed by this incredible woman in my life I let all the other areas of my life slide, and I neglected them. And this put a lot of pressure on the relationship that didn’t need to be there. 

This put a lot of pressure on my partner to be my entire social life and provide meaning in my life. It complicates things a lot when you do this. 

By the way, this can also spur on things and amplify things like retroactive jealousy, because, on some level, it heightens the anxiety, it heightens the unnecessary emotional investment that you’re putting in this person. It just puts all kinds of pressure on your partner and pressure on your relationship. And for me, and for many other people this can result in retroactive jealousy. 

Don’t make your woman your world, don’t make your partner your world.

On a related note: the third piece of advice that I would offer my 20-year-old self, is to spend more time investing in your male friendships, spend more time investing in your friendships in general. This goes back to the previous point, but it’s so important I really want to hammer this home because this is a big mistake I think that I made in my early 20s: not investing as much in other relationships in my life aside from my intimate relationship, not hanging out with my buddies as much, not going to the bar watching the game with them, and just having fun. 

Top-5 Relationship MISTAKES I Made In My 20's

Sometimes on a Friday night, I felt like I was getting all of my social needs met by my girlfriend at the time. And of course, an incredible partner can add incredible dimensions to our lives. And when we fall in love, they are filling all of these needs in our life, or at least that’s the way it feels because they’re our lovers. They’re our best friends. They’re our therapists. Sometimes it feels like they’re our parents. You get the idea…

But the truth is, we are social beings, and we need multiple relationships in our lives. I always think about that line by Esther Perell, the Belgian author who says,

“Nowadays, we expect one person to fulfill all of the roles that we used to expect an entire community to fulfill, an entire village to fulfill.”

Nowadays, we put so much pressure on our intimate partners to fill up our entire lives. This is such a mistake. And I wish I’d invested more in my friendships when I was in my early 20s. 

Another piece of advice I’d offer 20-year-old Zach: have more fun, let more things slide, stop taking yourself so goddamn seriously. Stop taking the relationship so incredibly seriously. And having all these intense discussions and arguments and drama and all this stuff. This is not to say “take relationships lightly and don’t care about people and don’t care about women and don’t care about your partner.” Of course, that’s not what I’m suggesting. But again, I think this comes back to the point I made earlier about feeling like I didn’t have as much time as I actually had. Because you’ll never be 20 years old, ever again, you’ll never be 24 years old, ever again, you’ll never be 30 years old, ever again. 

And the person you’re dating, when you’re 20 years old, is probably not going to be the person you spend the rest of your life with. For some people, that’s the way it works out. And if so, and you’re happy, that’s great. But for most of us in the 21st century, that’s not the way it works out.

Enjoy the relationships for whatever they are worth, have more fun, and stop taking it so seriously having all kinds of drama and crazy expectations.

Enjoy the unfolding of time, letting things happen as they’re supposed to happen, rather than putting all kinds of pressure on things to happen a certain way. Rather than having all these crazy expectations of a relationship, when you’re 20 years old, that that relationship is probably not going to fulfill. 

And finally, I would tell my 20-year-old self: love is not enough. Compatibility matters a lot more in a relationship than you probably imagine matters right now.

When we’re younger, we may feel that love is really all we need. Right? One of my favorite Beatles songs, “All You Need is Love. There’s a beauty and simplicity in that. And there’s a certain truth to that. 

But when it comes to relationships, things like fit, things like lifestyle, things like values, all these things are incredibly important. And if all you have is love–which, by the way, is often attraction and lust masquerading as love… but that’s another video. But when all you have is love that can lead you down some pretty dark paths, because again, things like lifestyle and compatible values and compatible family values, compatibility matters so much. 

Beware of the trap of thinking that love is all you need when it comes to sustaining a long term relationship over many years, 

One of the lessons I’ve learned over the course of my 30’s is that things like lifestyle and compatibility matter so much more than I used to think they mattered. And you can have an absolutely incredible relationship where love grows a little more slowly over time.

Top-5 Relationship MISTAKES I Made In My 20's

And maybe it doesn’t come in the form of some lightning strike at the beginning of the relationship where your hormones are jacked, but love where you give things a little more time to simmer. 

You give things a little more time to build. Love where you take your time a little bit more and pay attention to things like values and compatibility, which can be so much more rewarding, so much more satisfying, so much more fun than the experience of love I had when I was a younger man.

Zachary Stockill
Zachary Stockill

Hi! I'm a Canadian author and educator whose work has been featured in BBC News, BBC Radio 4, The Huffington Post, and many other publications. I'm the founder of, the author of Overcoming Retroactive Jealousy and The Overcoming Jealousy Workbook, and the host of Humans in Love podcast.