Difficult romantic relationships are common in college, with painful breakups often leading students to seek help from the college counseling center. However, these already painful situations are further complicated when one member of the couple refuses to allow the relationship to end. An area of particular confusion on the part of the college counselor is when to seek the Dean's campus equivalent of a restraining order. In the following we suggest the Dean's intervention can be both sensitive to the unique psychological struggles of a person in such a relationship and important to further the student's personal development. Several of Shakespeare's sonnets and the work of Jacques Lacan are used to further develop an appreciation of the obsessive dynamic. (Contains 1 note.)