"Waking Up With You" is a song by Waylon Jennings. The lyrics depict a person who is facing various struggles and challenges in life. The beginning lines describe the feeling of being lost and unsure of which direction to take, like a sail that's torn and unable to catch the wind. The phrase "a dollar short on a three dollar night" suggests a lack of resources and feeling inadequate. The person is turning left because they feel they don't have the right to make choices or go in the right direction. Despite these difficulties, the person holds onto a dream. The dream represents hope and motivation to keep going. They believe that maybe this time things will work out, but somehow the pieces just won't fit. However, they find solace in the fact that they always have this dream to hold on to, especially as long as they continue waking up next to their significant other. The song also highlights the idea that storms and hardships in life are temporary and will eventually pass. The person is reminded of this by their partner, who tells them that storms never last. The partner is seen as a source of strength and support, shining through like a silver lining in the dark clouds. The lyrics emphasize the importance of having someone by your side through thick and thin. The singer acknowledges that their partner will always be there, right or wrong, and together they will continue moving forward. This sense of companionship and resilience serves as a foundation for the person to hold on to their dreams. Overall, "Waking Up With You" is a song about facing adversity, finding strength in a shared love, and holding on to dreams as a source of hope and inspiration.