Tom is a bit of a waster...
Turning the wrong side of thirty hit him pretty hard, and what with having no money, no love life, no decent job prospects to speak of, and with debt coming out of his ears, well, the future wasn't exactly looking too rosy.
Still, he's a likeable chap, is Tom. He's the first person you'd invite to your party and likely the last one to leave. A little bit of your sensible side probably secretly wishes you were a bit more like Tom, actually.