@SteffRose,
Your boyfriend has some weird priorities.
Are you close enough to talk about his debt? College (even if he didn't finish) is one thing. Gambling debts or a bad spending problem is something else entirely. I am not saying you have to turn into the Morality Police with him, but it may make a difference to you, if he went into debt to entertain himself or improve himself.
As for the work pal, I take it your relationship is not known at work - at all, or just not by this coworker? If the coworker didn't know (and I am
not excusing his behavior at all), then I wonder what else your boyfriend is keeping secret. As for him remaining pals with this boundary-less jerk, I really have to wonder about that particular choice. If I were being bothered at work, my husband would maintain the barest level of civility with that person, in order to keep himself from being arrested and me from being fired or retaliated against. But he (my husband) sure as hell wouldn't be friends with the harasser. I am more of a priority to my husband than any 'cool friend' of his is.
You might want to start asking those kinds of questions.