Although she had been very successful in her schooling and in becoming an attorney despite some language processing problems, Loretta’s 40th birthday was upsetting for her because she felt like a failure for having ended a 4 year engagement and for her inability to sustain emotional closeness to others. She struggled with intense ambivalence about social relationships and, like many other adults with Asperger syndrome, her ongoing conflicts over intimacy led to a significant depression in midlife.