It is evident that we cannot entirely fulfill our ideals. Although less evident, it is also extremely difficult to always remain within the limited zone delineated by our boundaries. The Jewish sages knew that it is extremely difficult for people to comply with strict rules; they asked, therefore, that if such violations are unavoidable, they should at least be in discretion. Thus, Rabbi Illai the Elder taught that “if one feels that his passion threatens to make itself master over him, he shall go to a place where he is not known, put on black clothes and do as he pleases, but he shall not profane the name of Heaven publicly.”

The flexible nature of boundaries is indeed evident in love, whose significance makes the violation of boundaries "in the name of love" acceptable. As Rosa, a single mother, claims when interviewed for the book, In the Name of Love, “I have always been willing to take the kinds of risks involved in love; they don't really even feel like a choice. Love is always worth it.” In this view, violating boundaries is not necessarily an immoral deed. On the contrary, living by adhering strictly to such boundaries may be immoral, as it does not take into account unique, specific, personal and circumstantial features. In this regard, the philosopher Stephen Toulmin argues that “A morality based entirely on general rules and principles is tyrannical and disproportionate… only those who make equitable allowances for subtle individual differences have a proper feeling for the deeper demands of ethics.”

To decrease the violation of boundaries, we may want to make our normative boundaries more flexible, yet this in turn may weaken the safeguards against further violation. Take, for example, cyberspace where the romantic and sexual boundaries are much more flexible than in offline circumstances. This flexibility did not reduce the number of offline violations of boundaries but rather increased it. Romantic and sexual cheating increased with the expanded use of the Internet.

Another attempt for dealing with the deluge threatening to ruin our normative boundaries is the “zero tolerance” policy, which strictly prohibits any type of boundary violation. In contrast to this policy, which essentially disregards reality and hence, is extremely harsh and hard to adopt, a Scottish proverb says: “better bend than break.”

It is easier to draw clear boundaries than to keep them. As one woman remarks while telling her story on the Internet, “I found myself truly surprised that mere characters on a keyboard could carry with them such an erotic and emotional charge. But the guy was married and although we did establish ground rules, I ended up ‘coloring outside the lines’ in a way I never thought I would.” Normative boundaries are supposed to guide our behavior, but reality is more complex than what can be prescribed by simply marking dos and don’ts.

Guiding principles should provide general directions, such as “drive safely”, rather than specific rules, like “don’t exceed 100 kilometers per hour.” What constitutes safe driving may vary considerably, depending on several factors, such as the competence of the driver, the conditions of the road, and how other people drive. Similarly, romantic behavior may vary considerably, depending on personal and contextual features. Guiding principles have no precise boundaries, and hence there is no golden rule telling us when to violate and when to stay within the normative romantic boundaries. Cracking a few romantic boundaries is sometimes hard to avoid, as only dead fish swim with the stream.