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Article by Marshall Segal

Staff writer, desiringGod.org

Do you regret your dating history? 62% of Christians say yes.

Crossway recently surveyed seven thousand readers about singleness and dating. The data looks at our desires to be married, our levels of satisfaction in relationships, and the spiritual consequences of trends in our dating. The number that leapt off the page for me was 62.

Nearly two thirds of not-yet-married Christians express regret over previous relationships. That means the critical questions in dating are not just whom to date, how to date, and when to wed, but what to do when we get it wrong. And the reality is most of us get it wrong at some point along the way.

I started dating too young (11 years old). I dated too much (six serious relationships before I graduated from high school). I made too many promises and crossed too many boundaries. If I could take anything back or do anything over in my life, it would be in my dating history.

The regret we carry often feels like it weighs more than we do, but that’s because we’re not meant to carry it around with us, and certainly not our own. As I have wrestled with my own regret, two verses in particular have renewed and revolutionized how I process my failures and mistakes in the past.

When I Fall

I can remember exactly where I was sitting in August of 2008, wrestling with guilt and shame and regret over failed relationships and sexual sin, wondering if I would ever overcome my broken history, when a friend recited Micah 7:8–9 from memory:

Rejoice not over me, O my enemy;
when I fall, I shall rise;
when I sit in darkness,
the Lord will be a light to me.
I will bear the indignation of the Lord
because I have sinned against him,
until he pleads my cause
and executes judgment for me.
He will bring me out to the light;
I shall look upon his vindication.

I had read the words before, but I had never really read them. It felt like I was hearing the gospel for the first time all over again. The prophet feels the weight of his sin: “I will bear the indignation of the Lord because I have sinned against him” — real regret, real guilt, real shame. The next words are some of the most stunning in all the Bible: “ . . . until he pleads my cause and executes judgment for me.”

We sin against him; he pleads for us. He is the prosecuting attorney and our defense. And he’s never lost a case. If you are tempted to let regret eat away your hope, you have lost sight of who your God is. Micah writes a few verses later,

Who is a God like you, pardoning iniquity
and passing over transgression
for the remnant of his inheritance?
He does not retain his anger forever,
because he delights in steadfast love.
He will again have compassion on us;
he will tread our iniquities underfoot.
You will cast all our sins
into the depths of the sea. (Micah 7:18–19)

He does not linger over your past; he passes over your iniquities. He does not resent pardoning your sin. If you are his, he delights to have compassion on you. He does not keep a quiet log of your transgressions to hurl against you in court. No, he buries every forgiven sin, paid for in full with the blood of his Son, at the very bottom of the deepest sea. Never to be dug up by anyone ever again.

Two Kinds of Regret

Now, some regret belongs at the bottom of the ocean. Other regret needs to be nailed to the cross first. The apostle Paul, for instance, writes,

I rejoice, not because you were grieved, but because you were grieved into repenting. For you felt a godly grief, so that you suffered no loss through us. For godly grief produces a repentance that leads to salvation without regret, whereas worldly grief produces death. (2 Corinthians 7:9–10)

Worldly regret — grief over the consequences of sin that does not grieve the sin itself — ebbs and flows with what our sin costs us in this life, rising higher on the shore of our minds some days and less on others. Eventually it will fall like a tidal wave when death brings us to God. But godly regret — grief over the way we have ignored, rejected, and offended God — produces a repentance that defeats death and enjoys eternity. Godly regret longs for God to look great — first in forgiveness, and then in grace-filled righteousness (Psalms 25:11).

Does your regret about your dating history lead you to God and away from sin? We will never attain perfection in this life, but forgiven children of God are men and women who increasingly hate their sin and prefer righteousness. Are you grieved by your past mainly because of what your sin cost you, or because of what it cost Christ?

What’s Next?

The Bible does not tiptoe around guilt and regret. Isaiah saw a vision of God that revealed the wickedness of the prophet’s own heart. He cries out, “Woe is me! For I am lost; for I am a man of unclean lips, and I dwell in the midst of a people of unclean lips; for my eyes have seen the King, the Lord of hosts!” (Isaiah 6:5). Confronted with infinite perfection and power and justice, Isaiah is undone. Regret leaves him in a puddle on the ground.

But the God who calms the waves also raises puddles:

Then one of the seraphim flew to me, having in his hand a burning coal that he had taken with tongs from the altar. And he touched my mouth and said: “Behold, this has touched your lips; your guilt is taken away, and your sin atoned for.” (Isaiah 6:6–7)

Your guilt is taken away. Your sin is atoned for. If God himself has paid for our sins, and declared us guilt-free, we have no right to wallow in shame anymore. We waste so much time wishing we would have done it all differently — chosen differently, said differently, touched differently. God does not call us to redo yesterday, but to do something new today — because of his mercy, in his strength, and for his fame.

So what should you do? Isaiah “heard the voice of the Lord saying, ‘Whom shall I send, and who will go for us?’” (Isaiah 6:8). Is the prophet too ashamed of his sin to step forward? No. “Here I am! Send me” (Isaiah 6:8). Once filled with regret, now filled with godly ambition. Not wallowing, but witnessing.

Isaiah’s life has been given new purpose, direction, and hope. His past is about God. His relationships are about God. His broken, sinful, regrettable history has become a canvas on which God himself has painted unique, undeniable, incomparable beauty. Instead of throwing it away in guilt and shame, Isaiah frames and displays his canvas for as many eyes and hearts as possible.

Let your regret become another reason to tell someone about what God has done for you. Walk others on the path out of devastating worldly regret into the healing power of godly regret.

Dating with a History

If the holy, sovereign God can love you and use you despite your dating history, then you can learn to love again. When he leads you into another relationship, you don’t have to pretend like your previous relationships never happened. In fact, to cover your past is to hide the grace and mercy God has shown you — to minimize what he has done in your life — and to risk falling into the same sin.

If you will ever be truly happy in marriage, you (and your spouse) will need to resonate deeply and joyfully with this confession:

Christ Jesus came into the world to save sinners, of whom I am the foremost. But I received mercy for this reason, that in me, as the foremost, Jesus Christ might display his perfect patience as an example to those who were to believe in him for eternal life. (1 Timothy 1:15–16)

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