Connections 10.08.2023: Regrets, I Have (More Than) a Few

Matthew 21:33-46

Yesterday I let my fifteen-year-old son connect his phone to my car’s audio system so we could listen to his playlist on the way to the orthodontist. I didn’t expect to end up singing along with Frank Sinatra: “Regrets, I have a few, but then again too few to mention….” Our children never cease to surprise us.

I think ol’ Blue Eyes had it pretty good (or maybe he was delusional or in denial) if he only had too few regrets to mention. I have enough regrets that I can not only mention them but classify them into categories. There are the regrets that were active mistakes. There are the times I hurt someone, whether I realized it or not. There are the things I should have done but didn’t. Then there are the times when I know I was doing the best I could and it worked out okay, but if I had to do it again I’d make a different choice. Those are light regrets, but there are a lot of them and they are definitely mentionable.

In the parable of the wicked tenants (Mt 21:33-46), Jesus describes a landowner sending emissaries to collect the harvest; three times, the tenants beat and kill the owner’s servants and even the owner’s son. Jesus’s audience knows the landowner should “put those wretches to a miserable death and lease the vineyard to other tenants who will give him the produce at the harvest time” (v. 41).

Jesus quotes Psalm 118 and tells his listeners, the religious elite of his day, that God’s kingdom will be “taken away from you and given to a people that produces its fruits” (v. 43). If this audience isn’t delusional or in denial, they should be feeling the sharp pangs of regret, but apparently, if they have any regrets at all, they are too few for Matthew to mention. Even when they know the story is about them (v. 45) they don’t regret their role; they only seem to regret Jesus’s popularity. They regret that they can’t—yet—treat him the way the wicked tenants treated the owner’s son.

There is another category of regrets: the ones when God has offered us chance after chance after chance. The times when we have refused to give God what belongs to God. The times when we have ignored (or, worse, denied or mocked or threatened or outright harmed) God’s chosen messengers, and when we have not even recognized God’s own son.


  • Most of us (unlike, apparently, Sinatra) have more than a few regrets. Do you think regret can have a constructive role in our lives? When have you learned from a regret, then made a different or better decision as a result?
  • What regrets do you have about your spiritual life? When you think about your faith, can you pinpoint times when you mistook God’s messengers or God’s work? Was there ever a time when you actively worked against someone who you later learned was faithfully serving God?
  • When you read this parable, what is your reaction? Is there a part of this text that is convicting? Comforting? Challenging?
  • Do you need to recommit to tend God’s world and give God the harvest? Do you need to learn to pay attention to those whom God sends and to respect their role? Do you need to become more aware so you can recognize Christ’s presence, and more self-aware so you can recognize your own regretful actions?

Nikki Finkelstein-Blair is the lead editor of Connections. She is a graduate of Samford University and Central Baptist Theological Seminary, and as a military spouse has had nine (at last count) different hometowns in the past 20 years. She and her husband Scott and sons Sam and Levi live in the Washington D.C. area. In recent years, Nikki has written Smyth & Helwys curricula as well as devotionals for and Baptist Women in Ministry. She weaves clergy stoles, knits almost anything, and dreams of making her dreadful novel drafts into readable books. She blogs about faith and making things at


For further resources, subscribe to the Connections Teaching Guide and Commentary. Additionally, the Smyth & Helwys Bible Commentary series is a scholarly but accessible means for enhancing your study of each lesson.

Print Friendly, PDF & Email