Singles Advice - Singles Advice - Read about Christian dating and get advice, help and resources on Christian single living.

When is the Right Time to Ask Someone Out?

When is the Right Time to Ask Someone Out?

EDITOR'S NOTE: He Said-She Said is a biweekly advice column for singles featuring a question from a reader with responses from a male and female point of view. If you've got a question about anything related to singleness or living the single life, please submit it to (selected questions will be posted anonymously).


I am 18 years old, and a senior in high school. I recently broke up with my girlfriend that I had been dating for a year (neither of us were mature enough to handle a dating relationship). I thought that I would take a long break from dating and wait for the "right one".

However, a good friend of me invited me to this Bible Study small group, in which there was a girl that I have known as an acquaintance (and secretly had a crush on) for many years. Since I joined this small group, I have gotten to know her very well in the last few months. She and I get along and share many common interests (especially in the field of theology/apologetics). I would like to pursue a relationship with her, but I have a few doubts:

1. I recently (within a few months) broke up with my last girlfriend, and I am worried that this is just the result of loneliness due to that event.

2. She has not expressed any interest in me (as far as I can tell), other than friendship.

3. She had a previous experience with a guy who showed interest in her, and then she left him for someone else.

I am afraid to tell her how I feel, because of those issues. But I don't want to wait too long either. Should I wait? Should I act now? What should I do?


You recently broke up with your girlfriend because neither of you were mature enough to handle a dating relationship yet months later you want to pursue a new relationship.

What has changed in your life since then? In what ways have you grown over the last couple of months, which has matured you to the point of handling a dating relationship now? 

You’re in the last couple of months of your senior year of high school.  Many changes are about to take place.  You’ll be heading off to college, a job or a combination of both.  This can be one of the most nervously exciting times of your life.  Why spoil it by trying to push a relationship you might not be ready for?

As a youth leader, I recognize the amazing opportunity you have being in community with one another.  You can spend a lot of time with the opposite sex getting to know them, building a friendship and learning much more about each other than you normally would (in a relationship), within the positive confines of a church organization.

Especially if you or her are leaving home for college, I would suggest you don’t pursue a relationship but rather continue to spend time with your new-found friend in and outside of “sanctioned” group activities.  Get to know her as a friend and along the way get to know yourself.  Discover who God wants YOU to be.

Oftentimes young people try to mold themselves to be someone else - sometimes to be like their friends and other times to be like the person they think their “interest” will like. 

Seek Him and the person God made you to be. Trust He knows what’s best for you and your life.  As you grow closer to Him (and her in the process), you will discover whether you are ready for a relationship and whether she is the “right one.”


I love how you have been thinking through this decision. My first thoughts are that you are very young, and unless you plan on dating for marriage, I would not date—but rather continue to build friendships, allowing God to mature you a bit. If, however, you feel that it wasn’t a matter of maturity that broke you and your girlfriend up, and perhaps you two weren’t compatible, then by all means, start to date again. 

But your question is specifically about this one girl. You mentioned she has not shown you any interest but you haven’t either, right? While I do believe it’s OK for a woman to show interest towards a man and not wait on the man, she might feel otherwise and be waiting on you to make the first move. So, in this case, yes you do need to tell her you are interested in getting to know her better. And as in all relationships, there is that risk of rejection. On the other hand, you mentioned that she was in another relationship and left him for someone else. This is a behavior that concerns me. Now, while you didn’t share what kind of relationship she had with the first man, she may also not be mature enough to handle a serious relationship. So, in this case, I would continue to get to know her, allowing more time to develop your friendship. If another man gets in front of you then so be it. It was not meant to happen between the two of you. But if it was meant to happen, then more time as friends will only strengthen your future dating relationship.

You are wise in your concern. Allowing more time in all relationships is a good thing and shows a growth in maturity. 

Proverbs 9:9 Instruct the wise and they will be wiser still; teach the righteous and they will add to their learning.

HE is … Cliff Young, a contributing writer and a veteran single of many decades. He has traveled the world in search of fresh experiences, serving opportunities, and the perfect woman (for him) and has found that his investments in God, career and youth ministry have paid off in priceless dividends.

SHE is ... Kris Swiatocho, the President and Director of Ministries and Ministries. Kris has served in ministry in various capacities for the last 25 years. An accomplished trainer and mentor, Kris has a heart to reach and grow leaders so they will in turn reach and grow others. She is also the author of four books.

DISCLAIMER: We are not trained psychologists or licensed professionals. We're just average folk who understand what it's like to live the solo life in the twenty-first century. We believe that the Bible is our go-to guide for answers to all of life's questions, and it's where we'll go for guidance when responding to your questions. Also, it's important to note that we write our answers separately.

GOT A QUESTION? If you've got a question about anything related to singleness or living the single life, please submit it to (selected questions will be posted anonymously). While we are unable to answer every inquiry, we do hope that this column will be an encouragement to you. Click here to visit the He Said-She Said archives.

Image courtesy:

Publication date: April 27, 2017