I was recently given the opportunity to write an article for Arise Ministries, an organization that seeks to empower single moms. They suggested I address the following question:

How long should single divorced moms wait and get healthy before dating?

Firstly, I want to say that just asking those kind of questions is a good sign.

As far as the answer, I’m not sure I really have anything new to say. But that is perfectly ok, because I have learned that often we seek some new, life changing wisdom, when in reality we just need to do what we already know.

And chances are you have already heard this many times before:

You need to be ok alone before you can be healthy in a relationship.

So, I’m not telling you anything new, I just want to reiterate why everyone keeps saying this thing that you may so easily hear and ignore.

I believe most people have a God given desire to be in relationships. Your yearning to find someone to do life with is perfectly healthy. There are lots of benefits to being with someone and you probably think about how your kids would benefit. However, a desire can be good and healthy, but given the wrong priority it just doesn’t work. Most houses need roofs, but that doesn’t mean you build that first.

So, let’s explore why being ok alone is a necessary foundation.

If you are not ok being alone, then essentially you fear being alone. You will fear whether you can make ends meet. You will fear the pain of loneliness and the empty times where you have to face all the things you do not want to think about. You will fear the uncertainty. You will fear finding out who you really are. And so on and so forth.

Given more time, I could explain in greater detail, but just trust me on these two principles about fear:

Fear is the opposite of love.

When you act in fear, you often cause what you fear to happen.

If you are not ok being alone, then when you are with someone, fear they will leave you will prevent you from expressing that you matter. It will keep you from setting boundaries, being assertive and requiring that the relationship be healthy. Most people will treat you how you allow them to treat you.

Furthermore, even if the relationship is good and healthy, if you do not know that being alone is an option, then will you ever really know if you are in the relationship because you want to be?

Oddly enough, it was a teenage boy who said something to me once that I feel exemplifies how everyone should treat the dating process:

“I will do everything that I am ok with to keep the relationship.”

While this may seem simple and straightforward enough, it is fear that breaks the rule and causes you to do things you are not ok with. And that is how relationships are allowed to become unhealthy.

So, to answer the original question, everyone is different. I don’t believe in any set time. And even the concept of waiting until you are ok being alone is pretty gray. As you pursue that place of personal well being you will fall down, make mistakes and uncover whole new realizations about your issues and vulnerabilities. And, even when you still have work to do, exploring the dating world is ok because the bumps and bruises that come with it will just give you more experiences and insights on where you are in the process.

But first, you have to be alone until you are not afraid of it anymore. And only you can be the judge of that.

Dating is rough for a lot of people. I am no exception. There is so much stress, drama and awkwardness. And a lot of that stress we bring on ourselves due to our own expectations, values and assumptions. One of those assumptions that complicates dating is based on an otherwise very useful rational thought:

“If something is not working, then you need to change what you are doing.”

Trial and error for short. If we want something to work, then we keep trying until we make it work. This results in persistence, problem solving, adaptability and a whole host of useful character traits. It is the way we should approach most problems in our lives. However, I find that this attitude is often a cause of problems when it comes to dating and relationships.

Now, please bear in mind that like most pieces of wisdom, this one is not a 100% rule, but just a part of the puzzle to keep in mind. Of course relationships take work, persistence and adaptability. However, my point here is that people get so focused on making relationships work they sometimes forget to ask if they should be making it work. A sign of healthy relationships is that they make you a better person. But if you have to change or hide fundamental aspects of who you are, then maybe you are not in the right relationship.

Let me just go ahead and share my experience. I was a nerdy teen in the 90’s before sci-fi and video games were as mainstream as they are now. Back then, “nerd” and “geek” used to be far more of an insult than a description of your taste in media. I was also distinctly under the impression that most girls did not like those things at all. It doesn’t matter if that belief was right or wrong, it still limited me. And so I thought, if I want to find a girlfriend, then I need to hide those things about me to improve my chances of finding a girl. Sure, writing about those assumptions and conclusions now sounds ridiculous, but it seemed so rational at the time. I wanted to broaden my appeal to have better odds at success, so I hid what I thought was undesirable. I think that is a common attitude.

And then one day, I went on a trip to California and spent a few days with my female, adult cousin and her family. While I was there, they showed me their board game closet. I perused their sci-fi movies and heard stories about their weekly Dungeons and Dragons games with friends. This was the first time I realized that there were girls out there who not only put up with those hobbies, but loved them just as much as guys did. And that completely changed the way I thought about dating.

Before, I had thought that finding a girlfriend was like most problems in the world. Make changes to increase your chance of success. But now I realized that dating was like a lock and a key. If the key does not fit in the lock, it does not mean there is something wrong with the key and you need to change the key. That key just does not fit with that lock. I did not need to change myself to fit with what I assumed most girls wanted, I needed to unabashedly put myself out there, making clear what I liked and what I valued. Even if it turns off 99% of the people, it will attract the 1% that I fit with best. This was not an odds game, this was a matching game.

In fact, there more clear you are about who you are, the faster and easier the process will be. We mistake rejection in relationships to mean that something is wrong with us, when in reality it is just the process of elimination to find the right fit. Again, to clarify, if you are cruel, paranoid, have trust issues or other baggage, we all need to continually work on self-improvement. But if you are worried that your desire for a serious relationship, your religion, your politics, your values or your interests will turn people off, then realize, it only turns off the people who are not right for you.

At the end of the day, what almost everyone truly is looking for is a relationship with someone who knows the real you, intimately, good and bad, and loves you anyway. You won’t find that by changing who you are.