Oscar Wilde advised falling in love with yourself as “the beginning of a lifelong romance.” This thought doesn’t sit well with certain people. To some it implies conceit, to others a concession to never being loved by some marvelous other person. In fact, it’s nothing of the sort. To deal with life’s inevitable loneliness with as much grace as possible and as little pain as necessary, you have to fall in love, if not with the sound of your voice and the size of your thighs, certainly with your own companionship. This is nothing but being a good friend—to yourself.

What makes a good friend? Well, somebody who’s kind and funny and dependable and likes to do the things you both enjoy. Since the two of you—or, in this case, the one of you—-already like the same stuff, all you have to be is kind and funny and dependable.
Kindness is just love with its work boots on. You extend it to yourself by treating yourself as well as you treat other people. If you smile at strangers on the street, smile at yourself in the mirror. If you’d serve a guest something better than peanut butter out of the jar, do the same for yourself. If you’d tell a child that spilling milk is no big deal, tell yourself that when you spill wine. Even red.

As for funny, just have fun. The ha-ha stuff will make its way in. Teenage girls aren’t masters of wit and comic timing but they can giggle for an extended period because they’re willing to get silly and the culture allows it. Be willing to have fun and be funny, and don’t give a whit about who allows it and who doesn’t. A very funny person I know, commedian Wendy Spero, author of Microthrills: True Stories from a Life of Small Highs, tells how she once had an executive assistant job in a straight-laced corporation. To put some literal sparkle into the day, she would routinely add glitter to her boss’s reports and memos. He came to anticipate the diversion of sparkling specks in the midst of boilerplate boredom. His superiors didn’t get it. Their loss.

I used to think that laughter and fun were extras, like dessert. Now I believe they provide essential nutrients. You owe it to yourself to have some fun every day. No one knows what the future holds. The fun you have today goes into a memory vault where you can pull it out when you’re under a rain cloud like Eeyore in Winnie the Pooh. If you keep a journal, I suggest that you write every night at bedtime something fun that you did that day. It doesn’t have to be uproarious. “Saw a movie” works. So does “Drank bubble-tea” and “Did the crossword with my kid.”

Quite a few people, myself among them, are not innately gifted in the fun department. Playing makes us nervous. I recently saw how recreationally challenged I am when I took an improvisational comedy class through Chicago’s legendary Second City. It involved three hours of agonizing “games” every day for a week. I so wanted to quit, but I stuck it out. (When you write self-help books you do have to maintain certain minimal standards.)

In the class, we had to pretend to play catch with an invisible ball (“You know it’s coming to you through eye contact!”) and then heighten the stakes with an invisible dagger, being tossed simultaneously. All the throwing and catching and eye contact made my head spin because I was taking it all so seriously. I was not going to be stabbed. I wouldn’t even have to chase an errant ball because there was no ball. That’s when it clicked for me: play means letting go of what’s real (or what seems to be real) and living in another reality where even winning and losing are make believe. When you can carry that playful attitude into regular days, the rejections and disappointments that crop up are easier to respond to and bounce back from. And being alone is perfectly pleasant because you’re in such delightful company.

Dependability is showing up for yourself. Being in your own corner. You’d think we’d all do this as a matter of course but in the same way that we sometimes fail to be there for others—it’s inconvenient or we’re tired or over-scheduled—we go AWOL in our most basic relationship, the one with ourselves. Reporting for duty in this case involves taking care of yourself, sleeping enough, keeping your clutter down, and making time for things you like to do even when it requires editing something else out of your PDA. It’s living today in such a way that you can look back tonight and say, “I did a decent job of it.”

Dependability boils down to keeping the promises you make to yourself, and not making promises you aren’t prepared to keep. “I can only show up for myself in the sphere of what I can control,” says Susan Cheever, author of American Bloomsbury. “A lot of showing up is in small but estimable acts: being on time, paying the bills, saying ‘I’m not eating sugar today’ and then not eating sugar.” This kind of behavior results in self-approval and self-respect.

Once you have those, you’re more likely to see time spent with yourself as time well spent. Then you’re ready to experiment with planning an evening at home. This is not because you don’t have a better offer but because you’ve blocked out hours on your calendar to be with yourself and enjoy yourself in some splendidly singular fashion. Maybe you’ll rent a film with subtitles, or reread Wuthering Heights cover to cover, or deep-condition your hair and give yourself a facial.

After a successful planned evening of “home alone,” graduate to the date-for-one. You can go out to dinner and to a movie or a play (single tickets often end up being the best seats in the house). The idea is to have a good time and get over the notion that there is any stigma around not having a date or an entourage.
 
In case you’re worried about ill-effects that could arise from self-appreciation, let me assure you that falling in love with your own company will not relegate you to a life of unattached isolation. The opposite is true. You’ll be honing the kind/funny/dependable skills that will make every relationship in your life, romantic and platonic, richer. These aptitudes and the aura of confidence you’ll emanate will draw people to you—and they won’t be the needy types who are attracted to others’ Sturm und Drang the way sharks are attracted to the wounded. You can expect really terrific people to start to fall in love with your company. You just have to be the first to do it.