Your dream presents a rich tapestry of emotions and scenarios that may reflect your subconscious thoughts and feelings about relationships, support, and concerns for others. Let's break down some elements of your dream to uncover the possible meanings:

1. Ian and the Pool: Ian's sadness and your platonic date may symbolize your desire to support friends or colleagues. The pool can represent emotions or a social environment, and your reluctance to be pushed into the water might suggest a fear of being overwhelmed by others' emotional needs or situations.
2. The Tall Guy and the Toy Car: The tall guy handing you a toy car could signify a playful or youthful aspect of life, but it might also symbolize someone trying to navigate their identity (as indicated by wanting to appear straight). This could mirror your feelings about societal expectations or the complexities of relationships.
3. The Event and Decision-Making: The flyer for an event that requires a partner may reflect opportunities or commitments in your waking life that involve making choices about who to align yourself with. Your hesitation to immediately say yes suggests you are considering the implications of such decisions carefully.
4. Flashbacks and Support: The flashbacks about the tall guy's troubled past reveal an underlying theme of empathy—your instinct to want to support him stems from recognizing that everyone has struggles. His dangerous past may represent fears of being involved with someone who has unresolved issues, highlighting your caution in relationships.
5. Financial Situation and Support System: Your conversation about his financial troubles reflects your awareness of the burden that can come with helping others, especially when they don't seem to heed your advice. This may symbolize your own feelings of responsibility and concern for those around you.
6. Overall Feelings: The dream's drug-addled quality could indicate confusion or anxiety about your role in others' lives and the impact it has on you. Feeling frightened yet sympathetic toward the tall guy suggests a conflict between wanting to help and fearing the consequences of getting too involved.

In summary, your dream seems to be exploring themes of support, emotional boundaries, and the complexities of relationships. It might be beneficial to reflect on your waking life interactions and consider how you balance being there for others while maintaining your emotional well-being. Taking time to think about decisions and setting clear boundaries could help you navigate these dynamics more effectively.