Tired of Being Single? Ask These Key Questions Before You Start Dating

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Marti Pieper

As a woman, I had to ask myself some major questions. The first: Are you ready to date?

I had been single for 12 years after my divorce from my son’s father, and I got tired of the waiting period. I had to ask myself that first hard question. “Are you ready to date? Of course I thought, Yes, I’m ready.

The next question was this: Why are you ready to date? I realized I didn’t really have a good reason other than being tired of waiting.

Was being frustrated in the waiting period a good reason to date? As I learned the hard way, the answer is no. I knew at that time, I needed to do some soul-searching. Why was I frustrated in the wait? I was then led to read about Ruth (the book Of Ruth) and Esther (the book Of Esther). As I studied these two powerful women, I noticed they were busy in their wait. They stayed focused on advancing their living situation: working, preparing and remaining on assignment.


I had to figure out how I became distracted. There are a number of ways the enemy can come in with distractions. Life happens, and just one bit of emotion can usher the enemy’s lies into your thoughts. The devil can manipulate loneliness, fear and anxiety very quickly. We have to resist it. If we don’t, and we sit in it long enough, we will be seduced to look for relief in places we shouldn’t. This only takes our eyes off God, even if it’s in only one area of our lives.

God wants every part of our lives, not just some. I began to think, If I could share my thoughts, good days, bad days and everything in between with someone it would make my life better. I got tired of dealing with life by myself.

But the truth is, we are never alone. God is always with us. I believe I had to learn to walk and live in that truth so I could receive the wisdom I needed to move forward in the journey God had predestined for me. It is not easy at all, but it is possible.

The next questions I had to ask myself were these: Who am I? What do I like? What’s my bottom line?


We must know who we are. It’s not about what we do for a living or in ministry but who are we? What kind of man do you like? What are you willing to sacrifice, put up with or compromise about?

Before you date, these are major questions to ask yourself. I had never questioned my motives or my desires before, and I realized none of my answers lined up with the place I had grown into. The new me. The delivered me. The transformed me. The new wine now must be placed into new wineskins (see Matt. 9:14-17).

I was not willing to sacrifice the way I did in the past. I was not willing to water myself down for someone else comfort again. I had bottom lines and deal breakers now. I refused to bring old baggage with me. I was determined to walk differently to receive a different outcome.

Once I soul-searched and I answered the tough questions. I was prepared to take a chance with dating. I put myself out there. I left the four walls and discovered a whole new me. While I was discovering this wiser, cooler version of myself, I met some amazing men. There are ways to get past your fears and past disappointments, but you must take a moment to ask those tough questions. Believe me, waiting is challenging, but it’s not the wait, it’s what you do in the wait.


I am so glad God has set us free. We can truly have life and have it abundantly. We just have to take the honest steps and walk out of the old into the new. Dating is possible. Friendships are possible, and marriage is possible. Wisdom from God is the key in every situation.

For more from Dr. Gina on singleness and dating, listen to the podcast included with this article!

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