Woman Teaching Woman

How should Christians redeem their regrets over past decisions?

Recently, I posted a dating ad from a 39-year-old never-married single mother. She explained that she was now a Christian and was looking for a man to marry her, so that she could have a second child “the right way”. Some people thought we should take her conversion at face value. Others thought she was desperate and looking for a financial bailout. How can we tell if she is really sincere?

Well, I was still thinking about the comments on that post when I saw another great post from Laura, who writes at An Affair With Reason. Her post is about the feelings of regret that people have because of their past mistakes, and how Christians should deal with those regrets.

She writes:

As I thought about what to write I became distressed, sorrowful, angry, and even despondent over some of my own decisions. As I sobbed inconsolably, I noticed that every caustic thought began with, “If only….” That’s when I realized I was still carrying the burden of regret and I didn’t know how to let go. It wasn’t that I still needed God’s forgiveness or that I had any doubts about my standing with him; I knew I was forgiven. It was the lifelong consequences that I experience to this day which embittered my soul and squelched my joy.

The “if onlys” are a heavy burden to carry. They represent shattered dreams that will never be recovered in this life. They invoke feelings of discontentment, grief, and doubt. They cause us to sob with regret for what could have been, to pray for second chances that we know will not be granted.

So what do we do with the regrets that we must live with for the rest of our lives? Lately, as I’ve reflected on conversations I’ve had with many women who have made regretful decisions over the years and on the direction of our culture, I’ve noticed two very distinct paths:

1. Attempt to assuage our own guilt and regret by convincing others to make the same foolish, and even sinful, decisions we made.


2. Humble ourselves, grieve our losses, and commit to teaching the younger generations to choose a better way.

The first path is the wide and well-traveled one. Tragically and despicably, most people today seek to justify themselves and ease their consciences by getting others on board with their own ignorance, foolishness, and sinfulness.

She’s got quite a few examples of the kinds of regrets that men and women have, and different ways of dealing with those regrets. Some ways self-serving, others God-serving. Her examples are really interesting. It reminds me of “The Great Divorce” by C.S. Lewis, where he explains why some people don’t resist God, and others do. Some people want to justify the past, and keep making decisions to benefit themselves. Others want to serve God. They want to take on the difficult work of opening up to others, and loving them by telling them the truth.

When I hear someone with a past say that they have now become a Christian, I normally ask “is this conversion just convenient for you or is it the result of some process where your mind was changed through study?” You can ask the person to show their work – how did they get to the right answer? And what has becoming a Christian cost them? How does it affect their relationships with non-Christians?

People “convert to Christianity” all the time based on need. Sometimes they’re trying to get something for themselves, e.g. – wanting to not be judged for their past, so they can attract a partner to financially support them. But other people spend years reading books and changing their minds page by page, debate by debate. Then they put their knowledge into practice.

I have mentored women who did this. One girl who contacted me through the blog wasn’t able to talk to her smart atheist brother about her faith. Then, she read a bunch of apologetics books about science and history, then called me and slipped the phone into her pocket and let me listen to her make a bold, informed stand for her Christian worldview for two hours. She won every point.

When people really become Christians, they don’t do it in order to be happy and or to be liked. They take on work, and they take on shame, because they have a Boss now. That’s how you can tell that real repentance has taken place. The letters of Paul in the New Testament are filled with advice for Christians who want to be bold, put themselves second, and advocate for their Boss. You should read them. When you read the Bible, try to put aside your feelings, your desires, and your concerns about what people will think. You’ll find that putting work for the Boss ahead of what you want is worth the price of being “second”. I would start with Philippians, then go on to 1 Peter.

By the way, this isn’t the first time I’ve linked to Laura’s posts. Here are some of the other times I’ve linked to her work on my blog: on voting, on Islam, on mentoring boys, on fighting with pastors, on learning what works when dealing with atheists. She had a 10 part series advising women how to choose a husband, which really made me feel good as a man. Today, most people see a husband as an accessory – like a handbag. He’s there to provide, or to be a handyman, or to complain at if the wife is unhappy. Men should read that series, and find out what we can do in a marriage, if we are valued for our distinctive male nature.

One thought on “How should Christians redeem their regrets over past decisions?”

  1. The preacher in me wants to come up with 4-6 R’s.

    So let’s say “Christians … have regrets over past decisions.”

    1/ Repentance
    True Christians demonstrate contritution over sin (“I have offended God”) and desire to change their ways. They would not want to displease God and would want to “have a change of mind” even to say “God is right and I am not.” (metanoeo)

    It’s not just “being sorry about the consequences.”

    2/ Remission of Sin
    Christians are forgiven of sins. Psalm 103:12 ESV says, “…as far as the east is from the west, so far does [God] remove our transgressions from us.”

    God does not hold our terrible track record against Christians.

    There’s definitely things I remember from say, my childhood onwards that I think were bad decisions. Sure, some people might shrug and say, “You were just a kid” or whatever. I just remind myself these are forgiven sins and thank God and then use that as motivation for living for Him.

    3/ Redemption
    God has redeemed our lives. We should no longer live for ourselves, but for Jesus who died for us (2Cor. 5:15).

    It’s a transformed life. We no longer serve ourselves and our lives are no longer lived around giving ourselves pleasure, but we have a higher purpose.

    4/ Restitution and Reparation
    Sometimes we feel some degree of lingering guilt. But it would be the wrong thing to do to rationalize or to bring others into the mud.

    Instead, we should “do what is right.” Zacchaeus (in Luke 19) was not condemned for legalism — but rather, praised.

    What did he do? As a tax collector, he was supposed to collect monies from various people and whatever he collected in excess of what he had to remit to Rome he could keep. Tax collectors were effectively running a Roman franchise and had to submit their franchise fee — so many accused tax collectors as being in cahoots with Rome and the equivalent of traitors and extortionists, extracting money from people to get rich.

    Zacchaeus offered to give half his possessions to the poor and to repay four-fold if others thought he had cheated them out of that money.

    Saul of Tarsus went from being one of the most zealous persecutors of the first century church to being the most prolific writer and missionary for the first century church, the Apostle Paul. He went from going against Jesus — and very visible so — to turning his energies and intellect and efforts to advancing the cause of Christ.

    Liked by 1 person

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