How to Be Happy Alone (And What to Do When You Are)

How to be happy alone

The Situation

Since I was little, I had always latched on to one person. As a child, that person was my mother. As a preteen, I went from best friend to best friend. Once I hit 16, I was always in a long term relationship. I had never spent more than an hour alone in my life except to sleep. Is it any wonder that I was miserable unless I was close to someone?

Here’s my advice, based on my own experiences, to learn how to be happy alone. Want to skip my story and go straight to practical tips? Scroll down to the “What I Learned” section!

The Learning Experience

It wasn’t until my ex dated someone during one of our breaks (see How to Tell That It’s Time to End Your Relationship and How to Find “The One”) that I realized it.

When we got back together, I demanded that my ex compare me to that other girl in just about every aspect: looks, intelligence, behavior, you name it. I needed to hear from him that I was better than her.

He had come back to me after she broke up with him. Why was it so important to me that I was better? The answer that came to me was painful: because what I thought of myself depended directly on what he thought of me.

Now, I’m on the older side to be called a millennial. But my mom was a pioneer of the helicopter mom movement. If I didn’t walk the two blocks home from school right away when I was in junior high, my mom would drive around the neighborhood searching for me. (This was in the time before kids had cell phones.) She had to be standing over me any time I was doing my homework. And I had to give her the passwords to everything I did online. She didn’t believe that every kid had to have a trophy, though– I wasn’t doing well unless I was the best at everything. So I learned to have a fear of failure and fear of being alone– I was only doing well if other people were around and telling me I was doing well.

My religious family also taught me that it was a sin to be proud of myself or to think highly of myself. I learned that any positive thoughts about yourself had to come from other people. Whether that was the message my family wanted me to get, I’ll never know, but my pattern became obvious to me. I always kept around that one best friend who thought the world of me. When we’d fight, I’d do everything in my power to get them not to be mad at me. Eventually, they’d get sick of me needing constant validation and I’d find a new best friend to spend all my time with. And once I started dating, the same pattern happened with boyfriends.

Regardless of how it happened, I finally realized the problem and knew I needed to fix it. I needed to stop relying on another person to convince me that I was a good person. I couldn’t put that kind of responsibility on someone else anymore– all that did was lead them to finally resent me. And so I needed to be my own best friend.

I had no idea where to start. A self help book I was reading, Intimate Connections, suggested that I try doing things on my own. That seemed really desperate to me– I’d look like an idiot going to a movie or out to dinner by myself. The book explained that doing things on your own is more fun than it seems, and they had an experiment to try to prove it. Using a worksheet, I’d predict on a 0-100 scale how much fun I’d have going somewhere alone . Then, when I got back, I’d record how much fun I’d actually had.

I actually had to Google things to do on my own. I hated the idea of going out anywhere alone where people could see me. But if I was going to learn to be comfortable alone, I’d also have to get comfortable with the idea of other people’s judgements of me being alone. I’d need to learn not to care what other people thought of me because only what I thought of me mattered.

I started with a movie. And what I thought would be a horrible experience with people laughing at me turned out to be a pretty enjoyable one. No one even looked twice at me, and the movie let me forget that I was even alone in the first place. I felt great!

I had always been interested in watching Redbull’s Flugtag events, so I looked up this year’s. You could either go to the event live (downtown at the beach in the cold, no thank you) or watch it live at a handful of bars in the city. There was one at a casino fairly close to me, so I armed myself with a book and headed out with high hopes.

I waited hours, but the event kept getting delayed because of high winds. I nursed one glass of cider that whole time and read my book. I even chatted with an old couple who came to sit at the bar.

The bartender finally gave me the website they were using to stream the event and told me I could watch it at home. By the time I got there, the event had already started. I was a bit disappointed, but I was proud of myself for putting myself out there the way I did.

After that, a whole new world opened for me. I didn’t need someone to entertain me or take care of me. I didn’t need to check in with someone else to see if what I was doing was “right” or “good.” I wasn’t conceited just for loving myself. I could make my own positive opinion about myself and not feel guilty about it.

And once I learned to love myself, I was ready to form my first real relationship.

What I Learned: How to Be Happy Alone

Being happy alone takes two steps: changing your thoughts and changing your actions.

Learn to recognize your negative thoughts. You may be avoiding spending time alone because you believe mistaken ideas like “I’m not a complete person unless I have a significant other” or “Only losers have to go out on their own” or “If people liked me I wouldn’t have to be alone.” Once you learn that your opinion of yourself is the only one that matters, you may even learn to enjoy being alone, and other people may start enjoying spending time with you more. I’m not a medical expert by any means, but If you’re having trouble with self esteem, I’d suggest reaching out to a therapist or another mental health professional to help you through it.

Once you can recognize your negative thoughts, challenge them. Everyone knows the saying “fake it ‘til you make it.” The book The Confidence Code explains that if you’re faking it, you’re doing it. So try things you’re scared of. Predict how much you’ll enjoy those things before you go. Then, record how much fun you actually had doing those things. You’ll realize you’re having fun and not worrying about what other people think before you know it!

Try new things on your own. Here are a few suggestions:

  • See a movie.
  • Sign up for a fitness class.
  • Go for a walk (and listen to an audiobook while you’re at it).
  • Treat yourself to dinner.
  • Visit a museum.
  • Get a massage.
  • Shop at your favorite store.
  • Attend a creative class (writing, painting, ceramics, etc.).
  • Find a Meetup event that aligns with your interests.
  • Take a weekend trip.

Stop caring about what other people think. There’s only one person who can make you happy, and that’s you. Decide what’s important to you and do those things. Other people’s opinions shouldn’t come into play. While that’s easier said than done, if you continue to challenge how much fun you think you’ll have by doing things on your own, you’ll become more and more comfortable making decisions for you and no one else.

Have you learned to enjoy being alone? What are your favorite things to do alone? Let us know!

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About the Author: The Hard Way Learner

The Hard Way Learner is a 30-something corporate writer who has just finally started to feel like she’s got this adulting thing down. She lives in a condo in Chicago with her fiance and her cat, Catticus Finch. In her spare time, she loves to travel, absorb stories in any form (books, TV, theater, you name it), and give advice (requested or otherwise).


  1. Love this post! I’m also struggling with trying to do things on my own so this was a great breathe of fresh air; as well as, it feels good to know there are other people out there in the same boat as me. 🙂

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