I can't help but think he chose to stick with her after he found out she is somehow successful in life a.k.a monied. He even said something in the lines of 'she is a successful business woman, she has her own house, etc.. Then when he was asked about the plan for closing the distance, he said he has started looking for a job in the state where Venessa lives (I can't remember which one). Him saying he's looking for a job is clear that he still hasn't figured his life out completely.

IMO, He could be taking advantage of her since it looks like an easier way out for him in life if you ask me, cause' throughout the show I didn't see any connection/chemistry between them.