After The Break-Up: 7 Rules For Dating Myself (With Video)


One of my favorite things about CatholicMatch is the forums section. The message boards allow members to vent, make jokes, give advice, even share recipes!

Some time ago a wise woman commented in the forum, “The only common denominator in a string of unsatisfying relationships is you.”

In the meantime, that quote from the 70s hit me: “Women have become the men they wanted to marry.”

And of course, there was the adage that “no one can love you until you learn to love yourself.”

With these platitudes in mind, I thought: The only way to figure out how to find a good relationship is to have one…with myself.

So I set out to be my own boyfriend.

I started off this experiment the way I usually start anything – with wry humor. I had fun defending my decision to my friends: “I don’t worry about who pays! There’s no ‘third-date pressure! I’ll never get stood up!”

My friends also got a kick out of the cheesy love songs I’d dedicate to myself on Facebook.


Fun & games

I initially thought I’d solve my problems by dressing up, buying myself flowers and going places alone. But those are Band-Aid solutions. Those things are what another forum poster cleverly dubbed “topically applied romance” and they don’t get to the underlying issues.

I made it seem like I was embarking on a light-hearted adventure, but I knew I had serious work to do. I eventually understood that I was on a spiritual quest to see myself the way God sees me.

It didn’t start out that way.

For the first few dates, I was doing exactly what I’d been doing for years, either alone or in unhappy relationships: I’d zero in on happy couples and resent them, feeling jealous and left out.

But after a while I realized this wasn’t getting me anywhere. What a bad date I was being…to myself!

I then worked out a set of guidelines, despite my natural tendency to rebel against rules:


1. I was not going out by myself, I was with myself. I would not think of myself as single and alone; I was determined to enjoy my companionship as much as I enjoyed time with friends or loved ones.


2. The same attention and care that would go into getting ready for a real date would go into the time I’d spend with myself. It was important to signify the value I assigned to my own company.

As any woman knows, the time spent in front of a mirror before a date is not about vanity; it’s mental preparation. I deserved to look my best, with makeup and everything.


3. This was not a clever way of getting attention. I wouldn’t look around to see who noticed me if I was on a real date, so I wouldn’t do it with myself. I needed to appreciate myself, not put myself on display.


4. I would approach each date with a sense of optimism and a positive outlook. This was remarkably easier to do with myself than the real dates in the past. I was determined to have fun on my dates, and I did!


5. Related to No. 4, but not in violation of rule No. 3, I vowed to smile as much as possible at what moved me: passersby or passing thoughts. I used to see no point in smiling if no one received it. But now I needed to take in as much joy and delight as I could, no matter who witnessed it. I started smiling at the universe.

Not surprisingly, smiles were returned; they were everywhere!


6. I would not seek refuge in outside stimulus: no books or newspapers, no phone, no iPod, nothing to divide my attention. I would never check email, text a friend or read the paper on a real date. This should be no different.


7. My dates started when I left my apartment and ended when I got back home. There would be no quick, one-hour rendezvous with myself between meeting up with friends. Although this was something I sometimes did on real dates, I needed that sense of ritual to legitimize the time with myself.


The pleasure of my company

Beyond the list of external guidelines, there was a lot of internal work to do. I needed to learn why someone else would like spending time with me. In retrospect I was having lousy dates and seeking out lousy dating prospects because I was lousy company to begin with.

Not that I didn’t know how to be charming, make interesting conversation, and put my best self forward. It was a matter of burnout; I’d been through so many negative experiences, I had no hope that things would change.

I also silenced my internal monologue, what I call “The Relationship X-Ray Machine.”  The best way to do that was the best way to do anything: pray!

Praying for an outcome is not helpful, so my prayer was not something like: “Please, God, make the machine shut down and send me my soul mate now so that I don’t have to be dressed up in this fancy restaurant all by myself looking like a fool because I’m obviously single and alone.”

Instead, I thought about the beautiful words of St. John of the Cross: “Silence is God’s first language.”

I started to consider my dates as a practice of mindfulness, something I’d learned about from centering prayer and other forms of apophatic contemplation.

Being mindful means staying in the present in the most complete sense: slowing down and noticing every sensory experience in the immediate environment. Savoring a cup of coffee, for instance – really tasting the subtle notes of the beans, really seeing the exact shade of  brown, observing the column of steam rise from the mug, inhaling the heady aroma itself that makes coffee lovers far and wide go weak in the knees.

Mindfulness is, among other things, a practice of using the senses as a way into the divine. The conscious mind (the one that is bogged down with insecurities, memories, questions) is put to rest. It’s a tremendous relief. It’s also a tremendous realization of the beauty and love God provides us with constantly – if we open ourselves up to noticing.


Image and likeness

Lastly, it took a lot of self-talk to see myself as God does.

I’d managed to silence the RXM, but silencing my inner critic was a lot harder. I figured out that the second a self-critical thought came up, I had to consciously negate it with a positive affirmation.

When I berated myself for being seven minutes late to meet friends, I’d start to think, “but my friends are so happy to see me they don’t even care, so why should I?”

I then deliberately reviewed the reasons they were happy to see me, just to remind myself of all my good qualities.

It was illuminating – and more than a little painful – to notice just how often I had self-critical thoughts, particularly about things that were irrelevant. This is an issue I’m still grappling with, because I’d somehow become my own loudest critic and worst enemy.



I knew I had a breakthrough one afternoon when I took myself to one of my favorite parks downtown. I’d just bought a single Calla Lilly at a bodega and walked onto the lawn next to a pier overlooking the Hudson River.

The sun reflected off the river as a tour boat was making its way around Manhattan. The park was bustling with the after-work crowd; rollerbladers and bicyclists rested on benches. A dance troupe practiced the Tango on the pier. A sudden, gentle breeze ruffled my hair and I found myself teary-eyed with gratitude.

The sight of so many happy couples would have caused tears of despair a few months before. Once I realized what these tears meant, there was no stopping them; they streamed down my cheeks, ruining my carefully-applied makeup.

In silence, I dabbed my cheeks and gave God a tiny thumbs-up. I smiled at His universe.

At that point, I thought I was ready to date someone other than myself again.

As it turned out, I had a few more lessons to learn. But I never lose sight that being mindful is the way to recognize the perfect, unconditional, divine love that always surrounds us. Having received such an incredible gift, Saturday nights with myself became something to treasure, not dread.

Ironically enough, toward the end of my adventures in self-dating, I came across this video clip:


Naturally, I dedicated it to myself on my Facebook page, and shared it with all my single friends!



  1. Deepu-772853 November 23, 2014 Reply

    Beautiful and sincere writing that helps and uplifts. Thanks a bunch! PTL!

  2. Onyinye-730484 July 19, 2011 Reply

    So true! If you do not love yourself, how can you love some one else? You can not give what you do not have. In solitude do we really discover ourselves and our innate abilities as well as harness our skills or talents. Even in the bible, when God called a lot of people, he had to first of all separate them from the crowd before he could use them. Moments and periods when we get to be by ourselves, should be valued and used as opportunities for growth and self realization. According to the writer…’a period of mindfulness and realization’ .
    The world is too noisy, a lot of times, we’re caught up in numerous activities…Times of aloneness are precious!

  3. Arlene-637343 July 19, 2011 Reply

    Thank you for writing this. I think mindfulness is such a great lesson for everyone. Thank you for sharing how God has grown you so that others like myself, can grow too. 🙂

  4. Irene-704558 July 17, 2011 Reply

    Knowing yourself is always important in all we do. We can’t give to others until we give to ourselves. If we never think of who we are, what we like, what are blessings are, how can we be honest with anyone? What is a relationship without honesty?

  5. Janna-10421 July 5, 2011 Reply

    It’s important to remember we are made in God’s image, perfectly, wonderfully made. We must never become self-indulgent about this, though; we are made to serve Him. I wish the author could have mentioned, “If you want a friend, be a friend.”
    Go out and volunteer. Find like-minded people. Serve others. Go to Eucharistic Adoration. Pray for others who are suffering, because there is always someone worse off than ourselves. Offer up communion for lonely people. Talk to people at church, the grocery line, the bus stop. Make the effort to brighten someone’s day. Throw out compliments to service people. Let someone cut in front of you, in line or in traffic. And, yes, the author is correct: smiling is good for the soul.

    • Cate-291547 July 9, 2011 Reply

      Janna, you are correct. I did start to learn through this process how much of a friend I was NOT being to myself – always very critical and uncharitable towards my lot in life. Thanks for your wisdom!

    • Fatin-423187 July 9, 2011 Reply

      Janna, you are a great woman, i admire your comment alot !, you gave me a great start, God Bless you !
      it is very destructive to limit ourselves and to think that we can’t do anything if we don’t have apartner! Actually , may be we can do more ….. we can be light for other people and we can pray for other people who are suffering ….We can draw a smile on other’s people face and this alone can give us a great peace in our heart. There is a special wisdome that i like, says” if you want to cry, you will cry alone! but if you want to smile ,you will find the whole world smiling for you! “

      • Paul-716327 July 19, 2011 Reply

        I’m fortunate that I can walk to work each morning, my aim is to say “Good Morning” to those total strangers you walk by. It is a challenge that can be very rewarding.
        Thanks very much Jana & Fatin for your thoughts.

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