6 Ways To Be Ready To Pursue A Relationship



Anonymous asked (made anonymous by request) —

Hey brother, hope all has been well. Just wanted to throw a question at you, since I recall you telling me a bit about possibly proposing to a certain someone :]. Though currently this doesn’t pertain to me, I’ve always wondered about the specific things that a man should do when he has feelings for a sister in Christ. I’m not really talking about the tangible things, like how to talk to her, but more-so what he should do internally, on himself. Examples, what should he pray for, what should he be cautious with? Stuff like that. Hope all is well, God bless.


Thanks for asking this question the way that you did.  I think the “practical how-to” is really important, but it can become shallow and mechanical. I appreciate how you want to know the intangibles and internals.  That shows you’re already on the right path.

Since I know you might feel some pressure that you’re single, here’s a quote by Timothy Keller about that all singles need to hear —

“Being single allows the freedom to serve God in ways that a married person may not be able to with their concentration focused on their family. Also, this ‘gift’ of singleness may only be for a period of time. It should be embraced instead of being a struggle to rush into marriage.”

I want to be careful here that I don’t turn this into a magic formula, but knowing you, I am certain you will consider all this with deliberate care and thoughtful prayer.  This will also be a pretty weird list because I tried to work around the typical.  As always, please feel free to skip around.



1) Be okay with rejection.

If this lady doesn’t know your feelings yet, then I hope you’re okay if she friend-zones you.  I hope it’s cool if you just stay friends.  I don’t mean that you’ll be all chipper about it — of course it hurts to be rejected — but I mean, you won’t flip a table or sob about it for half a year.  That would convey a deeper fundamental problem of control issues or obsessive attachment.


2) Be prepared to confront yourself.

I think most advice on dating covers the initial phase of dating.  That’s probably the first three months, which is equivalent to learning Twinkle Little Star on the piano.  But after the blinding honeymoon phase is over, you’re going to find that you’re way more selfish than you ever dared imagine.  It’s a shocking rude awakening, and even after dating for nearly five years, I still find terrible selfish desires in my dirty messed-up heart.

It’s not your fault: it’s just how we are.  For all our dramatic pop-radio songs about “love is sacrifice,” no one’s naturally good at this.  It’s really hard to prioritize your life with someone, and when all the cuteness is over, it’ll feel like you’re killing a part of yourself to share life with her.  Be prepared to confront all the ugliness of your selfish soul.  I’ve known people who get married in their thirties, and they found it dang near impossible to give up their single-life habits. Think of your money, your time, your spirituality, your family, all the things you hold sacred: and you’re going to let another person into your territory with the raw power of a freight train.

Simply expect that you’ll be selfish and that she is not the enemy, and that will be half the battle.

My life verse (and the idea behind my blog and podcast) has been Psalm 139:23-24.  It’s the second passage I ever memorized (the first was Colossians 3:2).  David writes:

Search me, O God, and know my heart; test me and know my anxious thoughts.  See if there is any offensive way in me, and lead me in the way everlasting.

I pray through this continually.  It has been the most important personal Bible passage for my growth.  I pray it blesses you too.


3) Pray for continually strong friendships.

You’ll need a strong base of male friends (or female if you’re female) to keep you you.  I’ve seen dudes run into the nether void when they get a girlfriend and break off all meaningful contact with their friends.  They begin to set all their dials with their girlfriend, making the guy lose a part of himself down the line.  This probably sounds silly or sexist right now, but please believe me: your girlfriend cannot be everything you need her to be.  She can’t replace your same-gender friends, or else you’ll end up demanding all the wrong intimacy from her.  And if you think, “I’ll never be the guy that loses touch with his boys!” — you might be the guy most likely to do that.

Not all friends stay friends forever, because our lives and seasons change.  So pray that for each season, you have a strong community of friends who can both have fun and be willing to gently rebuke you.  And pray for a heart of humility that can hear the hard truth about yourself.


4) Seek a lot of wisdom and pastoral counsel.

It helped me a lot to hang out with old couples and married pastors just to observe what they were like together.  I wanted to see what was good and not good.  I asked tons of annoying questions.  I asked how they fought lust before marriage, how they melded personalities, how they argued things out, how they raised their kids.  I asked how God worked in their relationship.  We sometimes have a way of shunning older married people as “old-fashioned” or out-of-touch, but our elders are incredible fountains of wisdom that want to share what they know.  I’ve really been blessed by being nosy about their business, and they were always willing to pass on their knowledge.  They also helped me to sort out a lot of myths from the Christian subculture of dating.


5) Be ready to lead with confidence.

You’re going to be the spiritual tempo-setter in your relationship.  Whatever you think about Ephesians 5:21-33, I know one thing: I’ve never met a woman who doesn’t want a guy that can lead.  No woman willingly says, “Yeah, it’s fine if he sucks at leading.  I guess the kids that pop out of my womb can fend for themselves while my husband sits on the couch watching Dr. Who all day.”

Once a dude asked me, “But what if my girlfriend is spiritually more mature than me?  Why can’t she lead?”  After I stopped punching him in the groin, I told him, “Are you okay with your future daughter dating a guy who’s like that?  Don’t you think what you just said is more reason to step it up and not less?  Can’t you wake up, America?”

Confidence is not bravado or macho-manliness.  I don’t mean that you won’t mistakes or that you’ll be a perfect leader.  I just mean: Use this time wisely to pursue all the truth and wisdom and grace of God, so that you enter the fray with fruits blooming.  Your confidence comes from a complete dependent reliance on God, from whom you’ll be drawing all possible strength.  Anything else can’t give you the rock-solid foundation of confidence you’ll need for both dating and marriage.

I have to add here: Even though you’ll mostly be the metronome for the relationship, you cannot go faster than the woman wants to.  If you go too fast, you’ll end up coercing her into things she’ll only do to make you happy, and she will regret every second of it.  Once you cross certain boundaries, it’s hard to go back.  I’ve made my share of mistakes here too: so keep it slow and steady.


6) Pursue Christ and you’ll be just fine.

When we have a crush on someone, there’s a tendency to center our lives around them.  We make every song on the radio about this girl; we brush our teeth harder, use a bit more hair gel, and even change our boxers everyday.  I’m not saying this is wrong.  I’m saying: Please don’t let your heart stray into this sort of flex-to-impress mentality.  Your life is NOT about finding that special someone.  It has always been and always will be about living for the glory of God by the grace of God through the love of God.  Anything less is settling for less.

Regardless of how your dating life goes, the Gospel is still the most important thing about you.  Once you’re dating, the Gospel will continue to inform how you treat your lady, how you raise children, how you handle finances, how you confront the ugliness in your own heart — not to mention your eternity.  You already know that, but dating and relationships have a way of squashing us into myopic complacency.  We too easily forget about God’s mission and leave behind all that risk-taking, cross-bearing, self-denying passion.

Apostle Paul admonishes both married couples and singles to remember the urgency of our mission in 1 Corinthians 7, saying —

“For this world in its present form is passing away … An unmarried man is concerned about the Lord’s affairs—how he can please the Lord. But a married man is concerned about the affairs of this world … I am saying this for your own good, not to restrict you, but that you may live in a right way in undivided devotion to the Lord.”

I’ve seen a funny thing happen when men or women pursue God in the middle of a crush.  Sometimes they suddenly lose their feelings because they realize the crush was not really worth their time: and they find someone else along the way who is passionately pursuing Christ too.  I love it when this happens.  If you’re on the adventure that Christ has designed you for, then “Christian dating” is merely inviting someone to merge their adventure with you.  It’s fun, it’s electric, and it’s glorious.  So pursue God — and you’ll find others in pursuit.

I’ll pray you find a fellow traveler.

— J.S.

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