Tom's making a bit of a mess of this. There's the new woman in his life, except he's doing his best to mess that up. Then there's the unfortunate timing of the ex-girlfriend situation, which in all honesty, he could have handled better.
There's the fact that he he seems unable to form decisions without having a few beers first. And then after too. Plus he's taking advice from a distinctly dysfunctional group of mates.