Is being a single pastor an oxymoron?

This is a generalization, but overall I think we don’t really believe a single man can remain celibate. We don’t believe a single man can counsel a married couple or parents because he’s not experienced either situation. We’re suspicious of single men because of the apparent rise in child molestation cases amongst clergy. We think there is something ‘wrong’ with a guy who hasn’t managed to snag a wife by the time he’s 30. And if he is still single, he’s likely to have half the church trying to marry him off. We aren’t comfortable with perpetual singlehood.

I also think many interpret the verses directed at bishops and elders (the “husband of one wife” part) as being prescriptive rather than descriptive- as in he must have a wife rather than he is limited to one wife.

The author seems to assume that Jesus and Paul were pastors, which would make Paul sound inconsistent—if not silly—to state “husband of one wife” as a prerequisite for the office.
Of course, neither were technically pastors, nor were Timothy and Titus, Paul’s itinerant lieutenants to make sure his instructions were carried out.
While many single pastors may be talented or even successful, that really isn’t the point. Rather, it’s what we’re to do with passages like 1 Tim. 3 and Titus 1.

Husband of one wife is a character call to faithfulness (lit. a “one woman man), not a demand for marriage status. Demanding marriage creates all kinds of likely unforeseen issues. Besides the issue of Paul’s singlesness, those demanding marriage must retire all widowers, since they are no longer married.

Why is it that my voice always seems to be loudest when I am saying the dumbest things?

I was a single pastor for 1 and a half years, and my best friend who pastors in Michigan was a single pastor his first 7 years.

The argument about Jesus and Paul being single is that of the greater to the lesser. It is reasonable to believe that those higher up the chain also meet the requirements of those lower down.

The summary of I Timothy 3 is that an overseer/elder/bishop be blameless, and the rest of those term typify how blamelessness would be noted by observation. Certainly a man who has no wife or who has no children cannot be evaluated in those realms as one who does, but they must then be evaluated more heavily based on the rest of the criteria.

Blameless (which does not mean sinless) is the absolute criteria.

Here is some material on blamelessness from The Midrash Key (my book)
The Hebrew word for peace, shalom, is derived from the root word shalem, which means “wholeness and completion.” It is bound up with the word shlemut, perfection – the goal towards which we can only aspire. So to be “perfect” is to be at complete peace with God and others, at leas as much as possible. We are at peace with God when we are justified by faith in Jesus Christ and when we subsequently walk closely with him.
Yeshua knows we are sinners and can never be blameless in the practical, absolute sense. Does he make this seemingly unrealistic demand merely to convict us of sin and remind us of our depravity before God? Although we cannot prove his intent, perhaps part of his intent was to reinforce the idea that “all have sinned and fall short of the glory of God.” But, on the other hand, people can and do earn the title “blameless” in the Biblical sense, and I think Yeshua’s primary intent leads us in that direction. Individuals labeled “blameless” in Scripture are still obviously sinners. Thus blameless is not the equivalent of “sinless.” In some ways, the Biblical concept of blamelessness is exactly opposite of traditional Wesleyan “holiness” views.
And some relevant footnotes:
This thought suggests added insight to Paul’s words in Romans 12:18 (NASB), “If possible, so far as it depends on you, be at peace with all men.”
See Romans 5:1
Romans 3:23
The following are described in Scripture as “blameless:” Noah (Genesis 6:9), David (2 Samuel 22:24), Job (Job 1:1), Zechariah and wife Elizabeth (Luke 1:6), and even common elders were to be chosen on the basis of being “blameless” (Titus 1:6).
Holiness theology generally teaches that sanctified people are not exactly blameless because they make innocent mistakes, but that the sanctified are free from sin. The Biblical perspective, in this author’s opinion, is that mortals are always sinners, but sinners (who still sin) can be described as blameless.

"The Midrash Detective"