To the Harvard crowd, Fr. Orr's vigorous style was less endearing. It was perhaps natural that he did not share President Eliot's vision of Harvard Square, but he did not even answer correspondence from the coordinator of student religious clubs. One student, John LaFarge of the Class of 1901, was distinctly embarrassed by Orr, as he explains in a later reminiscence of the relationship between Orr and the local character John the Orangeman:

If John the Orangeman meant anarchy on a humble plane, Father Orr spelled anarchy on a lofty scale. It was just conceivable that some being like John might lurk in one of the discreet pews of the Appleton Chapel or even be found loitering momentarily in the corridor of the Fogg Art Museum. But by no stretch of the imagination could anything like Father Orr's sermons be conjectured in Appleton's pulpit nor would its staid walls ever echo to anything like his lurid descriptions of what he saw by night and sometimes by day occurring around his rectory in the rooming houses of Mt. Auburn St., not to speak of his hygienic discussion as to the effect that the taking of a "blue pull" (to rhyme with dull) is apt to have upon a pastor's health. One would have to go back to the early days of the Massachusetts Colony when pulpits were pulpits to find anything resembling the aspersions uttered by Father Orr upon the personal character of John the Orangeman when the latter presented his bewhiskered self for his Easter Duty in a state of general good will but of somewhat uncertain stance and step.

The relationship between church leaders, however, was apparently quite civil--Catholics contributed to the recasting of the bells of Christ Church and Fr. Orr offered a polite congratulations to the two congregations of the First Church celebrating their 250th anniversary in 1886. Catholic and Protestant clergymen united particularly in the "No-license" movement which banished saloons from Cambridge. By the end of the century, civic leaders took pride in "The Cambridge Idea," a blessing of religious tolerance and public goodwill.

After an initial decade of growth and expansion, the parish undertook its first burst of development in the 1880's, acquiring the cemetery on the Arlington line, building a school and substantially renovating the second-hand church. In accord with the instructions of the Third Plenary Council of Baltimore, many parishes were then building schools. In early 1889, the Archdiocese paid $17,000 for the estate of the late Gordon McKay, a wealthy sewing-machine manufacturer and Harvard benefactor, on the large sloping lot between Arrow and Mount Auburn. The Cambridge Chronicle reported on April 13 of that year that there was some doubt as to the disposition of the property:

At the time of the sale it was understood that a parochial school was to be erected. Later an idea has gone forth that it would be wiser to erect a new church building. The society has outgrown the present building at the corner of Mount Auburn and Holyoke Streets, and at the present date a new church will be imperative shortly. If a new church is built on the McKay estate it is probable that a school will be erected in connection with it.