Can you ask a girl out more than once?

Hey Sean,

    I like what you talk about in the book about being loving and doing all to the glory of God in terms of pursuing a relationship with someone. I also picked up that you were declined at least once to go on a date with your now wife. How do you persist as you did lovingly?  How does one do that lovingly? Gentlemanly? How did you do it? …. I have great pastors and access to sound wisdom from a myriad of other sources, but when you said your now wife turned you down, I really wanted to hear your thoughts.


Dear Romantic,

Thank you for your email. I am grateful for your humility and your desire to glorify the Lord in this situation. It is obvious that you are seeking him and want to be loving to this woman in your church. That is rare and I’m grateful for it.

You are also not alone in asking this question. Regarding my story, it is true that I asked Jenny more than 13 times to be in a relationship with me. But I must confess that my situation with Jenny is rather unusual. Jenny and I knew each other very well in high school and I didn’t pursue a relationship with her until after graduation. We had been in the same friend group and were together in numerous classes and extra-curricular activities. This is one of the reasons why I was so resolute after graduation. I knew that she was a godly woman and that I wanted to be in a romantic relationship with her. I had plenty of time to laugh, cry, hang out, and get to know her in a variety of settings over the course of three years.

After our first official date, I asked her to be in a relationship. I called it courting at the time. She thought about it for a little and then told me that she wanted to wait. I was going to Kentucky for school and she was going to Virginia. I knew that I had caught her off guard by asking her and that she wanted to focus on her bible studies and degree. Things were changing in our lives. I knew she was romantically interested in me, but the timing was off. She needed some space and I gave it to her.

Another interesting element to this whole matter is that we grew up in the same area. Each school break we would return home and be near each other. It was easy for me to ask her to visit and to check in on things. I would ask her to be in a relationship each time we were together and her answer was “No… not yet.” I was able to see that she was intentionally leaving the door open for me. She also allowed me to call her a few times a semester while she was at school and I would read biographies with her over the phone.

There was only one time that she told me that she didn’t want to be in a relationship at all and that was because she had just come back from a missions trip (was rather emotional) and decided she wanted to go overseas and knew I was going to be a pastor. That time was pivotal in our relationship and was actually really clarifying for both of us. That is a longer story and I can explain that later if it is helpful.

All of that to say… our situation wasn’t normal. I knew Jenny very well before asking her out on our first date and was able to know when she was putting down signals and when she wasn’t. I knew her friends and family very well. Jenny was allowing me to pursue her even though she was telling me that she didn’t want to be in a relationship at the moment.

When a girl says she doesn’t want to be in a relationship at the moment, it is typically because they are looking for a reason to turn a guy down gently. Spencer and I talk about this in our dating book and why it is best for a girl to be clear that romance isn’t on the table at all instead of using another reason to decline a date.

Regardless, I think the burden is on the guy (as a leader) to be able to discern what a woman means when she says “no.”

Here are some general thoughts I would offer:

  • Assume that when a girl says she isn’t interested right now that she means she isn’t interested in the relationship at all.
    • If she says she isn’t interested in the relationship right now, there must be an obvious signal coming from her that would give indication that she would want to be pursued in the future. With Jenny, she wanted me to call her. She looked forward to getting together each school break. She hinted that I should keep coming back later to ask her again. She asked me to pray about our relationship.
  • Don’t be afraid to let time and space enter into the relationship. If the girl is interested in you in the future, she will likely come back and give hints. She can find a way to be around you or have a girlfriend invite you over to her friend group for an event or something. Ruth and Boaz are a good example of this. Ruth found several ways to drop hints and signals to Boaz. Don’t try to force something and don’t be afraid to let time and space enter into the relationship. This will ensure that you are not too eager and it will give her time to decide further. This is also a good opportunity to trust Christ.
  • Don’t be afraid to ask for clarity if you think there is a real possibility that she might be interested. After allowing time and space, it is reasonable to ask for clarity. You can wait for an opportunity to talk with her in person and say “I know it has been a while since we talked last, but I would love another opportunity to take you out to coffee and get to know you more. I also know that last time you said that it wasn’t a good time to be in a relationship. I want to make sure that I honor you and I don’t want to put any pressure on you. Do you think now is a good season for us to go out to coffee? Or are you only seeking friendship in our relationship?” You can even acknowledge that these conversations can be awkward and you won’t be offended. You can always say, “I want to honor you as my spiritual sister. I thought the best way to do that was for me to tell you that I respect you, I’m thankful for you, and I want to let you know of my interest in asking you out. I won’t be offended if you aren’t interested in exploring the possibility of a romantic relationship. I want what you want and thought it would be best to ask you before assuming anything.”
  • Pray for wisdom (James 1). The Lord loves to give us wisdom and provide grace for all our dating awkwardness and mistakes.
  • Find some way to encourage her even if she turns you down again. Find one non awkward (and non romantic) way to encourage her as you would your sister after she says “no” again. If you don’t have a sister, think of ways you would encourage your mom. It could be like, “That is totally okay. I wanted clarity in order to honor you. Thank you for letting me know. As your brother in Christ, you should know that I really am thankful for your godly example at church and your joy in the Lord. I’m grateful to be church members and friends. Let me know if you need anything in the future and I will be praying for you. I’ll see you around next Sunday.” Or something like this!
  • If she turns you down again, for any reason, assume the door is slammed shut. Unless she takes initiative later or gives some obvious signal otherwise.

I hope this is helpful in some way. Thanks again for reaching out.

Regardless of what happens, I will pray for you that the Lord will cause his face to shine upon you and bless you and your ministry (Psalm 67).

Until then,

Sean


For more information on relationships and romance, check out Sean Perron and Spencer Harmon’s books Letters to a Romantic: On Dating and Letters to a Romantic: On Engagement, (P&R, 2017).

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