While on vacation recently, I was walking down the street with a newly acquainted co-traveler, when we were approached by a young Lubavitch Yeshivah student encouraging Jewish men to lay Tefillin. While this is not unusual, the student seemed intent on getting this person to put on Tefillin, and persisted in "encouraging" (really more like badgering and harrassing - much more than I expected to see or have seen before) after he'd declined more than once. But what struck me even more, was that the student then turned to me, after his own prodding had failed, and asked me to encourage my new acquaintance is this effort. Then, after I responded, "to each his own," (really in order to diffuse the situation and not because I am against Kiruv), the student looked betrayed.
Ultimately, I don't think the student engaged in a successful strategy, nor was his tact very pleasant. But the fact that he then asked me to pressure someone to do what he wanted him to do, despite the fact that the subject had already expressed disinterest and even discomfort, surprised me greatly.
In an age in which personal boundaries are regularly blurred (see social media, for example), religious freedom is a political wedge issue, and news coverage about bullying and peer pressure is nonstop, what do contemporary rabbinic leaders say about exerting social pressure on others to observe Mitzvoth?