Plane Truths & Homecoming Heartbreak

by Matthew Leonard
by Matthew Leonard

I totally thought I had a doozy of a story brewing. I’m talking planes, (dress) trains, and (convertible) automobiles.

What had started out quite terrible suddenly became unbelievably good. Incredible things were falling into place and I couldn’t wait to experience the adventure and share with you just how cool it is when God powerfully answers prayer.

Then things went crushingly sideways.

But through the whole process I was once again reminded of a very important, though often very difficult truth of which we all need to be constantly reminded. Here’s what happened:

As you may or may not know, I travel quite a bit to speaking engagements throughout the year. Generally, these events are set up well in advance. And as you can imagine, unforeseen conflicts sometimes arise.

Case in point…my daughter Lulu was elected to homecoming court about a month ago. I suppose it was always a possibility, but it took us all by surprise. She’s a talented, beautiful girl with lots of friends, but unless you’re nuts, you don’t pretend to understand the minds of teenagers or predict how they vote.

And, of course, homecoming was to take place when I was off at a speaking engagement in the South.

Now I don’t know what it’s like in your neck of the woods, but in the Ohio Valley, homecoming is second only to the Second Coming. It’s a menagerie of football halftime shows, pretty dresses, parades with firetrucks, convertibles, and children throwing candy to the cheering crowd gathered along the thoroughfare.

It’s a big deal.

And the father of the homecoming princess plays a large role (in addition to paying for the dress and flowers, of course). While mom actually does all the hard work of planning and execution, dad drives the convertible on which his daughter sits for the parade and walks his little princess across the football field at halftime.

And while I don’t generally live and die by school events, it was pretty tough for me to contemplate missing. I also knew it would be extremely disappointing to my daughter if I was absent. So I began desperately scouring the web for any flight schedule that would get me home in time (including airlines that normally you couldn’t pay me to fly.)

But alas, it was to no avail. Nothing worked. I felt miserable.

Of course, I had already begun praying…hard. (Gotta practice what you preach, after all.) In particular, I was asking Our Lady for a miracle. Surely she would understand how much I didn’t want to disappoint my daughter and miss this once-in-a-lifetime event.

And on the Feast of the Nativity of Mary, I received my “miracle.”

What was it?

Well, in the midst of the days leading up to homecoming, I had asked a dear friend in Florida to please pray for the situation. And only a few days before it was to all happen, she texted me the following: “OK don’t hold your breath, but my neighbor across the street is a pilot and owns his own plane…”.

This is the plane:)

Well, I did hold my breath…and kept praying.

And it worked! A very generous guy who doesn’t know me from Adam was moved by the New Eve to offer to pick me up in his plane. No joke. He was going to fly from Florida to Memphis, wait for me on the tarmac, and then race me to the little airport outside of lil’ old Steubenville, Ohio.

“Who does that”, you ask? This guy does.

I was so overwhelmed with gratitude (and still am)! My prayers for a miracle were answered! I’d arrive about 30 minutes before the parade and wouldn’t miss a thing! I was so happy!

But two days later storm clouds appeared on the horizon…literally.

Because of a hurricane, the plane owner informed me weather reports were dicey and there was the danger that we would have to go around the storm, which would delay me. “That’s okay,” I thought, “I can still make it for halftime.” While my wife was nervously picturing me in the lead role of Tom Hanks’ movie Cast Away, I was ready to roll…or fly, as it were.

So I kept praying and constantly checking the weather. “Surely this will work out,” I thought. “Look at everything that’s already happened. My prayers were answered on a feast day, for crying out loud!”

But alas, on the morning of the big day while I was preparing to speak in Memphis, the pilot texted and said it was some of the nastiest weather he’d ever seen and couldn’t get a flight path. We were a “no go.” After all the prayers, generous offers, and excitement, I was grounded.

My heart sunk. My miracle didn’t happen. I wouldn’t see my daughter performing her princess wave.

The weather report…

So after spending the day with the wonderful people in Memphis, I headed to the airport knowing I had little chance of even making an appearance at the end of the football game.

To make matters worse, my commercial flight was delayed and it took even longer to get home than I had feared. I missed it all. I can’t tell you how depressed I was on that flight. It was a low point, for sure.

And in the midst of the delays and such, I had a lot of time to ponder what the Lord might be doing through all of this. Because as I said, I was pretty down. It seemed everything had lined up perfectly. After all, it’s not every day that an incredibly kind stranger just offers to fly you here and there in his private plane, especially for a senior homecoming. So why did God pull the plug?

And the short answer is, “I don’t know…mostly.”

What I mean by that is that while I can’t tell you all the myriad of reasons God chose to do what he did, I know that part of it was getting me to really practice what I preach. Look, I teach the spiritual life. It’s both my job and my burning passion.

And one of the most fundamental truisms of the spiritual life is that we have to be abandoned the will of God. That’s the key. Whether it’s happy or sad or fun or hard, we have to practice trustful surrender to divine providence.


And that’s the lesson I re-learned in all of this.

Even when we beg and pray (and enlist the prayer of others), disappointments still happen. God is not a vending machine where we put in a few prayers, pull the lever, and get our bag of grace and a happy ending.

There’s a much bigger picture than what I can see.

And as a child of God, I have to trust that my perfect, loving Father is going take care of me in the most perfect, loving way. He knows what’s best, even if it disappoints me.

And part of the tough reality is that I may never know why it all worked out this way…at least in part. I can tell you that because I couldn’t make it, my father-in-law took my place. And when I saw him at Mass the following day, he was beaming. Forget cloud nine, he was over the moon after escorting his granddaughter in all her finery.

That took away a little of the sting. (So did the fact that when I told my daughter I wasn’t going to be able to make it, she said, “Well, it will be a good thing to offer up.” The Lord was teaching her, too, and she was listening. My fatherly heart was certainly warmed.)

But the reality remains that we live in a fallen world. Bad things happen. Yes, Romans 8:28 reminds us that God will work it all out for good, but that doesn’t mean it’s always in the manner we want.

And yet if we truly believe that he’s our loving Father, we have to trust that he’s going to work things out for the best in every single aspect, no matter if we see it now or not.

Yes, it might seem a bit silly that I chose to use homecoming court to describe how I was again reminded of our need to surrender to the Lord’s perfect will. I could just have easily used the example of my mother passing away from cancer or other more serious occurrences.

But as Romans 8 declares, “in everything God works for good with those who love him, who are called according to his purpose.” In other words, it’s not just the big stuff, he’s working through every moment, every circumstance of our lives because he loves us so much.

So while I didn’t get the miracle I wanted, I got the lesson I needed. And trustful surrender is a lesson we all need.

God bless you!


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38 Responses

  1. Thank you for the lesson! I need to practice abandoning myself to God and his love in every situation, thank Him for everything, and to not worry about how everything will turn out. Easier said than done, right?

    1. Matthew, this is a great example of trusting in Our Lord in a special event in your life and then giving it all to Him.

  2. Nice story Matthew… and Mother Mary gave it the college try. Our Holy Father had other ideas for learning. Stay well and God Bless!

  3. Sometimes letting someone else do something that you REALLY want to do, something that is your RIGHT to do, and giving that other person the joy of doing it is even more delightful than doing the thing yourself.

    It may not have been about you at all, but about God wanting to give a beautiful gift and memory to your father-in-law and your daughter – something extraordinary; something neither one of them would ever have dreamed of or expected to share. Sometimes when we think we’re the star in the drama, it turns out we’re just a bit player and God’s spotlight is really on someone else. Our only role is to be to step aside graciously and let the other person bask in the light.

    Your father-in-law was given a beautiful gift by God. You were just the UPS guy delivering the package.

    1. I agree with Nel!! Her response says it all. By the way, matthew’s daughter is truly beautiful and her spirituality sounds as if it is too.

  4. Wonderful point to ponder. My desires even good ones aren’t always going to happen. The lesson is how I handle the disappointment and still praise God for he’s goodness!!!
    Thanks Matthew for another life’s lesson!!🙏🙏🙏

  5. Thank you for the honesty. Your story has given me more hope and trust in a good and just God, than a lot of other prayer answer stories I have heard in the past. I really like your ministry. Blessings on all you do and all you are.

  6. It’s wonderful that we can always pray & trust the good Lord.
    Right now I am having a difficult time about something that has happened in my life, but Jesus is really teaching me a lesson that I must wait on the Lord. I have to remember that God’s time is not the same as my time.
    Matthew thanks so much for sharing.

  7. Dear Matthew.
    What a great lesson. I am a grandma to kids this age.

    Funny, because at my age I think that all the hoop d do regarding homecoming and prom and all the focus on this in high school is emphasizing the worldly too much.

    Hey! My own daughter was a homecoming princess also and I remember it well. All good.

    But—as I look back, and see our current world, I see the emphasis is on self and “me” is way too much.

    That is why I personally reject Facebook and Instagram.

    Your daughter is lovely. You are a great dad.

    But honestly how important is it to get to the homecoming ceremony?
    (If it was her wedding or something, that would make more sense😊)

    Seems that God may have wanted the kindness and special moment to be given to grandpa who (I believe could have been asked even if you were there!)

    We often get caught up in the cultural stuff that is fun and nice but in the larger realm of things does not really matter as much as we think.

    Frankly now, I wish I had focused more on having the kids giving more to the needy or old or sick, poor etc.
    Maybe emphasizing things like mission trips and helping others in town who cannot afford the basics.

    I am guilty myself especially when I was younger, of trying to make sure all things went right for my daughters. I found out it’s ok when they don’t.

    I think it was quite alright for you not to have things go your way in this case. Trying to be that perfect dad. I relate. It always backfires for me too.

    It also was good I believe, that God intervened and said no.
    God almost ALWAYS has other plans.

    So God got His way…and
    as a result a beautiful heart thing happened between a grampa older person and his precious younger grand child.

    That was sooo special for your daughter and grandpa!

    Enjoy your travels for the Lord and thank you for sharing.
    God bless you.

  8. What a beautiful story! What a gift you gave your father-in-law and daughter, a memory they will always treasure.
    I am so grateful to you for humbling yourself to God’s will and letting Him teach us about the Science of Sainthood through you!! Life makes sense now🥰

  9. Thank you for your lovely story. God showed you that he heard your prayers and He did perform a miracle for you, even though it didn’t all work out perfectly in the way you had hoped. Your response in abandoning yourself to God’s Will in your disappointment, your daughter’s response when you told her you would not be able to make it, and your seeing how your Father-in-law was beaming and was appreciative of the gift he had been given to share with his granddaughter, are all encouraging examples for us on how to accept God’s Will in our lives. Thank you again for sharing
    Your daughter was glowing and looked absolutely beautiful on her special day.

  10. Wow Matthew, what a lesson the Lord is teaching you, thanks for sharing, now we can all learn from your experience that whatever we want nothing is more important than following God’s will !

  11. Absolutely perfect, using homecoming as an example, Matthew!
    We all need to be reminded that our humanity, in this case your fatherhood, is not something to be dismissed off hand, but has value and meaning, and heartfelt desires.
    It’s how we deal with it (in you and your daughter’s case, admirably) that matters.

  12. Thank you for sharing this difficult story, Matthew. And, as always, thank you for your spiritual leadership.

  13. Wow what a lesson!! Funny thing is you’ve been recently deeply on my mind, and in my prayers, and I have been restudying surrendering to God’s Will! Of course I kept failing and getting annoyed and yelling, (yes, I was yelling!), at God for all the little misfortunes coming my way. Guess both of us needed to relearn that lesson!! I think the Lord was having a pretty big chuckle at my temper tantrum, (He realized the depth of my remorse shortly after the yelling session and had a good laugh), and was smiling gently at you as He fixed what needed fixing, (and really blessed your father in law and daughter!), and just gently reminded you who’s boss. Thanks for sharing this. I really needed the extra lesson push! God bless you and your entire family.

  14. Thank you for your wonderful story. Many times I have wondered the same. Why God lets things get to a certain point and then things go a different way. Recently I found this quote from C.S. Lewis and it is so fitting for the times we are living in.

    “We are not necessarily doubting that God will do the best for us;
    We are wondering how painful the best will turn out to be.”

    His best was painful for you and your daughter but it allowed His best for your Father-In-Law. Thank you so much for sharing.

  15. Matt, this is beautifully written. We were riding that emotional rollercoaster with you throughout the weekend! This isn’t about (perhaps) the overboard pomp and circumstance surrounding Homecoming, this is about the love that a father has for his daughter. You bent over backwards to be present to Lulu, while remaining faithful to your commitment to speak. I was standing next to Lulu while she got to facetime with you on your sister-in-law’s phone. You were with her. But more important, your Heavenly Father was with you, His precious child. He was feeling that same fatherly love and anguish for you that you were for Lulu. He orchestrated the amazing answers to prayer that could have gone without a hitch. Yet He allowed the storm to come. We don’t know why the story turned out that way, but I have to believe that permitting you to experience that disappointment wasn’t easy for Him either.

  16. Hi Matthew,

    Thank you very much for sharing your beautiful story.
    It’s always fascinating reading your story and books.
    I’ve learned now, that whatever experience we encounter
    in life, we leave it all to God, the Almighty.
    He knows what is best for us.

  17. Hi Matthew,

    Thank you very much for sharing your beautiful story.
    It’s always fascinating reading your story and books.
    Yes, I’ve learned now, that whatever experience we
    encounter in life, we leave it all to God, the Almighty.
    He knows what is best for us.

  18. Hello Matthew, beautiful story, beautiful daughter and a beautiful lesson for you and all reading this story. I have put a short message from St. Francis of Assisi. I think you have done well. Your daughter, now knows your heart. May God bless you and your family.

    “We cannot know the patience and humility of a servant of God, as long as all his wishes are gratified and all his wants supplied. But when the time comes that those around him conduct themselves in the opposite manner, then it is that we can judge of his patience and humility by his conduct.” – Saint Francis of Assisi

    We are not called to be successful, but faithful to the Lord.

  19. Hi Matthew, a beautiful story, a beautiful daughter and a beautiful lesson for you and for all who read it. Your daughter now knows your heart is right were it should be. We are not called to be successful, but faithful to the Lord. Like Jesus if we are faithful we will accept His Will. You have done well

  20. This is so heartwarming! For someone who needed a spiritual lift this morning, this reminded me of trusting the relentless love of God. I will remember this line- “And as a child of God, I have to trust that my perfect, loving Father is going take care of me in the most perfect, loving way. He knows what’s best, even if it disappoints me.” Thank you and God bless you, Matthew!

  21. Thank you for sharing Matthew. I remember participating in a novena of surrender… God the Father. I discovered that surrendering to Yahweh is not an automatic thing. It’s a deliberate, intentional choice we make everyday. Surrendering was hard at first for me. It’s easier and faster to make my own choices. Submitting to the will of the Father, surrendering all things to Him is grace in itself. This act brings us closer to Yahweh, helps us to obey Him in all things.

  22. Thank you Matthew for sharing this story which shows the love of a father’s heart for his beautiful daughter. I have learnt that even in the most disappointing and painful events in life, thanking God for the situation releases his grace to bear the suffering caused even if the situation does not change. God can be trusted.

  23. Dear Matthew,

    While I’m sorry that you and your daughter didn’t get to spend Homecoming together, God gifted Lulu and her grandfather with time to create special memories together -time that they might not have had otherwise.

    I broke my left ankle in a freak wheelchair accident in June of 2014. My father, who lives in Vermont, drove all night to be by my side when I woke up in intensive care the next morning. He was with me every day for the next month, staying at the home of family friends, and reassuring my husband, whose own circumstances made visiting me in the hospital logistically difficult.

    Even after he returned to work, my Dad continued to commute from Lyndon to Philadelphia by car, seeing me through another unexpected surgery (when he snuck his computer into the recovery room and we watched Jerry Lewis in “The Nutty Professor” together – My nurse came over, winked, said “I didn’t see anything” and left) and attending bi-monthly meetings with my medical team. It’s been that way every day of my life, but until then, I’m afraid that I took his presence for granted.

    As much as I wish I hadn’t broken my ankle, went through two surgeries in six weeks, or endured the seemingly endless pain, I now realize that in His infinite wisdom, God used the circumstances to give me time alone with my Dad that I wouldn’t have had otherwise; after that, the combination of distance, work obligations, and my youngest brother’s cancer diagnosis in 2017 made it physically impossible to see him in person for long amounts of time before Covid was ever a thing.

    What an awesome and wise God we serve!

  24. Matthew, what a great lesson for any parent. I am sure your daughter(who sounds so mature) understood all the effort and prayers you put into this miracle. She seem deeply spiritual as well and so lovely. I suggest you check in with the place you spoke at and ask what was the results of your talk. Never know, someone needed to hear what you had to say.

    Wonderful lessons learned.

    Thanks for sharing. Veronica G

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