Dreams about dating and emotional experiences can often reflect your current feelings about relationships, abundance, and self-worth. Here are some key elements to consider from your dream:

1. The Date: This symbolizes your desire for connection and intimacy. The unusual seating arrangement may suggest that you are stepping outside of your comfort zone or experiencing a unique situation in your life.
2. Emotional Release: Shedding tears of happiness indicates a sense of relief or joy in your waking life, possibly related to a recent achievement or a newfound sense of abundance. This can also signify emotional healing or the importance of expressing your feelings.
3. Abundance: Your ability to buy desserts without concern for the price suggests that you are reaching a place of comfort and security, both financially and emotionally. This may reflect your aspirations and current state of mind regarding your resources and opportunities.
4. The Desire to Squeeze: Wanting to squeeze her can symbolize a deep longing for closeness and affection. It may reflect your yearning for deeper connections in your life and an appreciation for the people around you.

Overall, this dream may indicate a positive shift in your life where you feel more secure and open to forming meaningful relationships. Consider how these themes of abundance, emotional expression, and connection resonate with your waking life and what steps you might take to nurture these feelings.