A number of years ago, I read a blog by an anti-Catholic Protestant apologist. The Protestant had been raised a Catholic, but (according to him) "found Jesus," "got saved," and was spending his time writing anti-Catholic screeds to inform Catholics why they didn't have Jesus and would be going to hell. The blog was fairly entertaining, when read from the perspective of a recently minted Catholic "grunt" apologist seeking to earn her stripes by dissecting and analyzing anti-Catholic arguments. Only once did a post of his truly anger me.
In this post, he mentioned that he had just returned from the funeral of his mother, which had been a Catholic Mass because his mother and the rest of his family had remained Catholics. To his credit, I don't recall him speculating on his mother's current location in the afterlife, but he did exult over having been given the opportunity to "evangelize" his Catholic relatives by ambushing the priest, who had come to comfort them, with all sorts of objections to the Catholic Faith that the priest was not prepared to answer. He evidently felt confident that the priest's inability to debate him would be the lever he could use to pry his Catholic relatives from the Church.
While feeling sympathy for this Protestant on the loss of his mother, I couldn't help but seethe over how he had exploited her death as a means to rattle his relatives' faith. I also couldn't help but feel empathy for the priest. While we must "always be prepared to make a defense to any one who calls [us] to account for the hope that is in [us]" (1 Pet. 3:15), a priest can be forgiven for not being able to summon the eloquence of St. Irenaeus (whose apologetics magnum opus was titled Against Heresies) over the casket of a deceased parishioner with all her relatives gathered 'round.
I was reminded of this blogger's post yesterday when I received an apologetics call from a Catholic. She explained that she had offered a lapsed-Catholic friend to have Masses celebrated for the friend's deceased father. The friend thanked her for the offer but said he didn't think it was necessary because his father was a good man and he was certain his father was in heaven. The caller wanted information she could give her friend to show him he was wrong in assuming that all nice people go directly to heaven with no need for purgatory.
I appreciated my caller's concern for helping her friend understand what the Church teaches on purgatory and the efficacy of Masses for the souls of the deceased. My concern, though, was that she was not dealing with a hypothetical debate over whether a good man needs Masses said for the repose of his soul. She was dealing with her friend over the repose of the man's own father. To press on with demonstrating to her friend why he was wrong in believing his father was in heaven might lead her friend to think that she was impugning his father's memory. That certainly was not her intention, but people do not always accurately intuit our intentions.
My recommendation to her was to drop the debate; have the Masses offered for her friend's father's soul; and trust that there may be some future time and place in which it would be appropriate to let her friend know that the Masses had been said—and perhaps also to resume the discussion over the efficacy of Masses for the dead.
In his famous exhortation to Christians to be ready to defend their faith, St. Peter added an important caveat. He said the defense we make must be done "with gentleness and reverence."
Perhaps he had in mind examples of Christ's own gentleness and reverence to people who may have needed correction but were also hurting. The woman at the well, who was living in an objectively sinful relationship with her putative husband (John 4:7-42), was stunned that Jesus would even talk to her at all, much less do so with the face-saving gesture of acknowledging her "husband" to be her husband until she admitted otherwise (verses 16-17). The woman caught in adultery was told "Neither do I condemn you" before she was told not to sin again (John 8:11).
Truth is important. But the one who is Truth demonstrated that the only way to share the Truth is with love (cf. 1 Cor. 13:1-13).