Dreams about being naked often symbolize vulnerability or feelings of exposure. In your dream, being naked in a pool while making out with your high school boyfriend may suggest a longing for past connections or unresolved feelings from that time in your life. The presence of your current partner's anger could reflect fears of betrayal or guilt about your current relationship, even if those feelings are not consciously acknowledged.

Sitting down for dinner with your parents and facing disappointment from everyone might indicate a fear of judgment or a desire for approval from those you care about. This part of the dream could signify anxiety about how your actions, whether in the past or present, align with your values or the expectations set by your family.

Overall, this dream might be urging you to reflect on your current relationships and feelings about the past. Consider what unresolved emotions or conflicts might be influencing your thoughts and actions in your waking life. It could be beneficial to communicate openly with your current partner about any feelings of insecurity or nostalgia you may have.