It wouldn't be careless of me to assume that the songs on Sleeping with Strangers all came from a place of heartbreak, and the disintegration of a relationship. On every song, we feel Jim Wolf's melancholy over lost love. The title track is a sad slow lament on having to start all over again against your will. Wolf sings "And I don't wanna know what you're doing/'Cos I want you back when this blows over/And you know we are only Sleeping with Strangers/'Cos we don't know how to sleep alone." Wolf has a talent for explaining the multitude of feelings that go along with heartbreak in such uncomplicated words. His lyrics are neither groundbreaking, nor particularly innovative, but it is this innate simplicity that allows for the songs to have such resonance with the listener. On "San Diego Sun" Wolf is almost berating himself: "Conflicted memories, can I get a grip/I can't believe I'm not over this." Wolf's knack for songwriting lies in explaining complex human emotions in such a straightforward way.

The production on Sleeping with Strangers is at times slightly over-polished and somewhat reminiscent of John Mayer, while additionally Wolf's voice occasionally borders on blandness. At times it feels like he is purposely restraining himself, rather than just letting loose and singing from the heart. However there is such a likeability and truthfulness to Wolf's songs that makes the music an enjoyable listening experience. Some of the album's stronger tracks, "House of Cards", "San Diego Sun" and "It's Life", are very evocative of The Wallflowers, in the sense that these songs are highly accessible and appealing, but also manage to be memorable and inviting of subsequent listens. At times, there does feel to be a bit of an over-saturation of sad songs about lost love, but that is actually one of the strengths of the album. It is honest in its self-pity, Wolf doesn't sugarcoat his feelings or try to reign them in for the sake of repetition; he wallows in his unhappiness, he is clear in his intent to document the break up of a relationship that clearly impacted on him very strongly.

Overall, Wolf has crafted a very strong album full of the sadness, loneliness and bitterness that is inherent in relationship breakdowns. Sleeping with Strangers is a likeable, relatable album with a clear focus, and an inherent understanding of what it is to be heartbroken.