Dear Father John, I have a question… My brother’s graduation is this March during Lent and my family normally eats in a really nice restaurant for dinner after graduations. Is it okay if we aren’t able to fulfill our Lenten fast or penance on days like 
that?
What a beautiful question! It shows that you are sincerely concerned about living Lent well. Since Lent is a season of special penance, prayer, and almsgiving (by which we prepare ourselves for the liturgy of our Lord’s Sacred Passion), you are wondering if it is possible to celebrate an important event without tarnishing the spiritual atmosphere of the season. I have three thoughts for you.
Keep Fridays Well
First, remember that we all abstain from meat on Fridays during Lent. This is a form of penance and self-denial that the entire Church engages in. We also take on personal penances and spiritual disciplines, but this is one we do as a Catholic family, united with all our brothers and sisters throughout the world, and throughout the centuries. So, if your graduation dinner were to take place on a Friday, you would actually need an official dispensation from this Lenten requirement in order to serve and eat meat.
Time for Celebration
Second, remember also that the Church has not removed all of its liturgical solemnities from the calendar during Lent. St. Joseph’s Day and the Annunciation often fall within Lent. Likewise, Sundays are still liturgical solemnities all throughout Lent (which is why Lent, which starts on Ash Wednesday and ends on Easter Eve, still has only 40 days – if you include the Sundays, it would be 46). On solemnities, the Church is able to celebrate the triumphs of our Lord without spoiling the Lenten atmosphere.
Equilibrium over Legalism
Third, if someone’s birthday or anniversary were to fall during Lent, that would be no reason to forego a celebration. I think the case you present is similar to those. The graduation is a real achievement, and ought to be celebrated. To have a special celebration in honor of the achievement is a good and just thing to do. You can celebrate wholeheartedly on that day, without giving up or compromising your Lenten disciplines of prayer and penance, and you may even be able to combine them. For instance, you could give the graduate a Lenten-esque graduation present, like a donation in his name to a Catholic orphanage or educational institution. That would show appreciation both for your brother’s achievement, and also for the spirit of self-sacrifice that Lenten almsgiving is meant to express and foster.
I hope you can see that the mind of the Church in this matter always focuses on more than simply following specific external rules. It sets aside these weeks as a time to turn up the intensity of our quest for intimacy with God, our Creator, Savior, and Lover. If we followed all the “rules” perfectly, but didn’t engage actively in that quest, we would be missing the point. Lent is a season of spiritual renewal, of spring cleaning for the soul. The specific rules and practices that the Church requires and recommends are all meant to boost us in that primary, interior, and crucial spiritual adventure.
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Art for this post on whether or not special events can be celebrated during Lent: Partial restoration of modified Invention de la sainte Croix par l’impératrice sainte Hélène (“Invention” [Finding] of the Holy Cross by the Empress Saint Helena), Winter de Saverne, 1839, Ralph Hammann photographer 2012 own work, CCA-SA 3.0 unported, PD-US author’s life plus 70 years or less, Wikimedia Commons.
