Insecurities, Red Flags and a Change in Ideals Dilemma 1 poses the question of doubts and comparisons. We delve into the insecurities that come from dating someone and being the opposite to their usual type. Dilemma 2, all things family dynamics and how to navigate difficulties like your partner being TOO close to particular family members. Finally, Shona and Shaan ask each other some in-depth questions based on their own dating ideals and how different things have become in this day and age.