5 Reasons NOT to Ask Him/Her Out

In Dating, Relationships, Single by Debra Fileta23 Comments

“I can’t get him out of my head.”

“I feel like I’m falling in love with her.”

“God told me I was going to marry him”

“I just have this feeling that she’s the one.”

I’ve receive a lot of emails voicing these type of concerns. All from men and women wondering the same thing: should I take initiative and let him/her know how I feel?

If you know anything about my perspective, you’ll know that in the proper context, I’m a huge advocate of men and women taking responsibility for their lives and ownership of their relationships by taking next steps. Because frankly, I think getting “led-on” has just as much to do with the follower as it does the leader.

But when it comes to initiating a relationship, here are 5 times you shouldn’t make the move:

1. Your relationship is not reciprocal: This year I asked my readers to tell me what their biggest relationship mistakes were in 2014. One of the top answers was this: getting involved in one-way relationships. So often, we’ll do anything for love, including taking a risk on a relationship where we end up doing all the work. Giving, loving, initiating, planning, forgiving- without getting anything in return. Have you been showing all the interest and doing all the work? If yes, say no to one-way relationships this year by getting involved in relationships with people who are giving just as much as they are taking.

2. You don’t know enough about him/her (or you don’t know enough about yourself!): In every relationship, there are two people you have to get to know. The first of those is yourself. Do you know who you are? Have you taken enough time to look in and deal with your hurts, habits, and hang-ups? If yes, then ask yourself this, do you know enough about him/her? I truly believe that a huge portion of relationship problems stem from the fact that we enter relationships without knowing enough about the person we’re entrusting with our hearts. Build a friendship, observe the person you’re interested in, and be sure you have a good idea of what you’re getting into. And if nothing else, give it time! Time will always begin to reveal a person’s true colors. So learn to wait…and watch. (Check out our free quiz: Are You Ready for Love?).

3. You’re seeing red flags: Yesterday a woman commented on one of my posts that “strong relationships can change people”. I had to wholeheartedly disagree. One of the biggest relationship problems comes right down to this: we give relationships too much power. Relationships can’t heal us, change us, or fix us- because they were never meant to. Before you get into a relationship you have to realize that it is what it is. Those bad habits aren’t just going to disappear for “love”. Those character flaws and personality issues won’t magically go away. If you see red flags now, you’re likely going to see them forever more because there is nothing you can do to change your partner- they have to seek change for themselves. If you see red flags it’s a sign to step back- not to move forward. Be on the lookout, you’ll save yourself some major heartache in the end.

4. You don’t have the approval of friends and family: We live in a culture in which we tend to do relationships in isolation. The moment a couple gets together, all of a sudden everything they do is “exclusive”. I find that rather dangerous, because this kind of exclusivity can keep some KEY people out of your life. People who you trust can often provide invaluable perspective and insight into your relationship as they’re observing it from the inside out. I’ll never forget the time in college when my dad pulled me aside and told me some concerns he had with the guy I was dating at the time. Thankfully, I allowed my parents and friends to freely speak into my life- because you know what? They were SO RIGHT! I was blinded by infatuation, but my dad’s words stuck in my mind until I started realizing that he was right. I eventually had the courage to let go, and move my life into a better place, and as a result, a better relationship. Don’t make choices in isolation. Check in with the friends and family you trust the most, and allow them to speak into your life as you consider moving forward in relationships.

5. You haven’t prayed about it: Why we wouldn’t take the advice of the Almighty God who knit us together in our mother’s wombs and knows everything about who we are and what we need is absolutely beyond me!! (Sorry for the run-on sentence, but I had so much to get out!). Prayer is so powerful when we’re looking ahead at our love-life! Sometimes the answer is clear. But sometimes it isn’t so clear. But there’s always an answer- even if it’s simply “Wait”. The beauty is that sometimes God answers us in unexpected ways. In fact, I’ve realized that sometimes God uses THEIR lack of interest to guide us in the right direction. At one point in my life I was SO discouraged by how much I was praying, and how little interest I was receiving from the guys I was interested in. Looking back, their lack of interest was an answered prayer in disguise. God spared me from relationships that I would have quickly moved into had the opportunity come. Now that I’m happily married to the love of my life, I’m so thankful God kept my heart from going places it wasn’t intended to go. So pray, listen, and obey. If you do, I guarantee, you won’t go wrong. (8 Ways to Pray for Your Love-Life – Or Lack-thereof)

Sometimes we’re called to take risks and move into healthy dating relationships, but other times, we’re challenged to take a step back and wait. If you feel like you’re in a place of waiting right now, don’t be discouraged! God is using this precious time in your life to continue preparing you into the partner he wants you to become. Embrace it, and hold on to the truth that there are greater things to come.

For more on experiencing God’s best for your love-life, pick up a copy of True Love Dates!

Debra Fileta is a Professional Counselor, national speaker, and author of True Love Dates: Your Indispensable Guide to Finding the Love of Your Life21 Days to Jump Start Your Love Life, and 21 Days to Pray For Your Love Life – where she writes candidly about dating, relationships, and how to find true love. You may also recognize her voice from her 150+ articles at Relevant Magazine or Crosswalk.com! She’s also the creator of this True Love Dates Blog!  Connect with her on Facebook or Twitter or book a session with her today!

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23 Comments on "5 Reasons NOT to Ask Him/Her Out"

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Debra, I can’t tell you how much I enjoy the way you word things – so wise, yet so practical ! Of course, trying to apply it to everyday life is difficult but never, ever give up, right? The “God told me I was going to marry him” made me chuckle…not because God won’t/can’t speak to someone or impress that on their heart but so oftentimes, we can fall into the trap of wishful thinking. I know I have told myself similar things: “If he isn’t the One, why can’t I stop thinking about him?! It must be a sign… Read more »
Melinda Galloway

thank you for sharing this wisdom Debra. I reaped a lot of heartache by poor choices in my youth, but with time and the grace of God, I am in a good place now. I do pray your readers will take your Godly advice instead of learning the hard way. Blessings 🙂

Hi Debra, thanks for this post….It hits home. I was guilty of 3 of the 5 things you write about in a previous relationship and how did it end…..me nursing a heartbreak at the moment. But even through my pain, confusion, and lonelines. …I know that God is still God and he is able to use that situation to bring glory to his name. He has been showing me a lot of things including where I went wrong, painful yes…..but definitely wiser too. So to everyone who has made these mistakes in the past, remember that God is present in… Read more »
OMG, I can’t believe I didn’t read my email to see this post before I shoot that text! Ackk!!! I just couldn’t take it anymore so I fired a text today to casually asked about a dinner offer that he had asked me about a year ago to see if it was still on the table. This guy has been in my mind for like 3 years and I just wanted it to go away. So I figured if I get openly rejected that that would give me the answer and I can move on instead of wishing, hoping, praying.… Read more »

This is just on point… Thanks Debra once more for sharing. I’m thrilled about this post. But particularly about the family/friends aspect because sometimes people are made to believe that ‘exclusivity’ is the best way. But I personally believe that God can use those around us to open our eyes for good.
I trust God to use this post to help more people in their relationship lives.
Once again thank you and God bless you.

Bracha Maoz
I have an adopted daughter who was adopted at a later age. Broke her engagement just 2 months before wedding. Both came from dysfunctional families. He is a young pastor a very godly man and she us a very beautiful girl who was very godly as well. He us very much in love with her and believes it was from God. After they broke she backslidde and because she is very beautiful men are always after her. She says she still loves him but believes that he is not strong enough for her. She says she needs someone strong. Is… Read more »

Thank you. Was encouraging.

“… sometimes God uses THEIR lack of interest to guide us in the right direction.” I absolutely needed to hear this. A while ago, I was getting so much proposals that my mind was clogged. I got tired of telling them off especially with some being adamant and so I asked God to steer away anyone who wasn’t the right person for me. But as they say, be careful what you wish ’cause you just might have it. Not only did some of the guys I had no interest in withdraw, the very person I really liked became distant and… Read more »
Ellen Mema Lomay

Wooow wonderful. God bless you Debra

Hi Debra, I took the quiz for the second time wondering what it would say compared to before. The first time around (a year ago?), was red according to the email I got. This time around it was yellow. I’m not totally surprised by that. The past couple of years have seen a lot of changes since coming out of an abusive situation. Having done the recovery program, counseling and reading (lots! of reading), I am in a much better place and have gotten to the point where I’ve ended friendships that were not what I wanted in my life.… Read more »
shirley D

Thanks Debra for sharing I totally agree with all those points. You inspire me daily to pursue purity, righteousness and fully depend on God in everything I do


so helpful! God bless you


This was spot on. So glad you shared this. I hope and pray that one day you can be just as famous and popular as these no experience, and unlicensed “relationship guru’s” out here.
It saddens me to think these people are leading people astray. I pray that God gives you the platform your so deserving on to get your teachings and leadership out here to the masses. We certainly need it, and we need you.

Thanks Debra.


Hey Deb,always on point!
I thank God for giving you Godly wisdom and understanding.your such a blessing to the Kingdom.

Thanks,needed this.


Wow! So helpful Debra! I’m here spending time with the Lord and crying out to him as i feel overwhelmed and your teaching came so handy and clear as GOD Intended for me to hear and reassure me that HE is with me and to continue to patiently WAIT for the one he has for me! You’re great and thank you so much for helping others! God Bless You 🙂

Luke Urban

Thanks for this Debra. I really wanted to rush into a relationship recently for the sake of getting into one but it was not reciprocal. I feel like God was telling me to wait though I struggle with waiting for who God has for me at times. At 29 years old, it gets hard trusting God has someone for me but I need to remind myself singleness is a gift in the season he has me single.

Sal Gomez
I don’t think that people realize how often this happens to men as well. I have met woman after woman after woman, Christian women, who fit all or some of these Reasons. The bible tells us to pray without ceasing. I pray even before meeting a woman. I’m only talking about Christian women here. Yet, I run into more problems with them, unfortunately, than secular women. Maybe because every single Christian woman thinks of you only as to whether or not she would marry you. Secular women don’t bat an eye at just going for a walk, or having a… Read more »
Emily D.
This is good. I can’t say enough for prayer in a relationship (and that’s an understatement) because when I knew that God was impressing a young man on my heart, I prayed for months before confiding in a couple of key people (being primarily my mother). I asked God, “When will this happen, Lord? Should I do something to get things happening?” He gave me a few words: Be patient (this came with a fresh wash of Holy Spirit hope and assurance). Trust Me and My timing. Don’t pursue him, pursue Me. It’s been an interesting year, and I am… Read more »