Alone But Not Lonely: 5 Tips For Enjoying A Night Out By Yourself

By: Karen Bigman

Image Source: Unsplash

After two years on my own I can safely say that I'm comfortable being alone. I've been fortunate to make more new friends post-divorce than I did during my entire 25-year marriage, but that doesn't mean I don't have more alone time than I used to. I have to admit it wasn't always this way, and it isn't always easy. However, with the right mindset and tools you, too, can master "the art of being alone" without feeling lost.

There are a lot of challenges for anyone post-divorce, especially after a long marriage where your life revolved almost exclusively around your children and your ex. There was always someone to bounce ideas off of, someone to help with big decisions about life and kids, someone with whom to share the financial burdens, and, of course, a standing date for Saturday night.

As married people, we expect to experience these things. But when that standard operating procedure for your life disappears and you begin to absorb the enormity of going through life without it, the thought of doing so can be paralyzing. Rather than forcing yourself to embrace a new community and find new hobbies and new friends, newly divorced individuals often end up becoming very friendly with Apple TV.

It happened to me.

While I was always independent − able to travel alone, eat at a restaurant alone, strike up a conversation with anyone -- without the security of a partner, all of a sudden that confidence was gone. How was I able to do this with such ease in the past but the idea of it now made me feel frightened and like a loser?

It took some time, but I realized that by staying in and being anti-social I was only making matters worse. After all, how was I ever going to get out of my "rut" if I didn't get out of the house?

For my first evening out by myself, I decided I was going to make a reservation for one at a hot new restaurant and ask for a seat at the bar. I got dressed up, put on my makeup, and high-tailed it downtown. My reward? I was seated at the worst seat at an empty bar. But that didn't stop me. I promptly moved myself to a better seat, took out some writing I was doing, and got comfortable.

As I perused the menu and enjoyed my first cocktail, the restaurant started to fill up and the bar got busier. At that point, the bartender asked me to move to a worse seat to make room for two people together. Now, I likely had a bit of a chip on my shoulder being nervous about eating alone, but I still wasn't going to move. I stood my ground and I felt empowered as a result. As the night went on, I ran into an old friend, ended up sharing my dinner with him and his friend, and had a most delightful evening. Point, Karen!

When I think back on that night, trying to figure out what it was that gave me the strength to eat alone, I realized it was my attitude. All I wanted to do was eat a good meal in a nice atmosphere. No more, no less. I wasn't looking to meet anyone. Had I gone with a different goal, perhaps the vibe I would've given off would've also been different.

Now that I've been going out on my own for almost a year now without a partner, I have a few pointers that help:

1. Plan on doing something other than staring at your phone. Bring work, a book, your sketchpad, or whatever will keep you productively occupied.

2. Don't be shy. Be friendly and exude confidence. Chat up the bartender. Ask him or her what his or her favorite drink is to make or what he or she likes best on the wine list.

3. Be conversational with the person or people sitting next to you if they seem amenable to it. Say something about someone else ("Isn't her ring amazing?" "You seem to know the bartender..." "Anything you recommend?").

4. Leave a generous tip. You will be remembered for it! Isn't it better to walk into a place where they know your name? (Remember the TV show Cheers? "NORM!")

5. Make the best of it! If no one talks to you, read your book, do your work, and enjoy your meal. Next week you can try a new neighborhood.

By doing these simple things, you can begin rebuilding your life one meal at a time. So check out Yelp for restaurants and ask yourself where you will be dining tonight.


Karen Bigman is a Life Transition Coach specializing in divorce. For more information on divorce coaching, visit or email