I have a coworker who's been with his girlfriend for two years, and honestly, the girl is unbearable. She's controlling, possessive, and I can see my mate going out with us less and less. Should I say something to him or just keep quiet and let him figure it out on his own?
Don't tell him anything unless he asks you directly. If he finds out you've been criticizing his partner, he'll feel like you've betrayed him and he'll probably pull away even more. The best thing is to keep the door open: invite him to hang out, show him that you value him, and if at some point he confesses that something isn't right, then you can listen without judgment. People need to figure these things out on their own, even though it hurts to watch him go through it.
The risk of staying silent is that after some time, when they finally break up (and they probably will), your friend is going to feel like you abandoned him during the period when he needed you most, without even trying to be there for him. The ideal thing is to keep the door open: keep inviting him to stuff, treat his girlfriend well when you see her, but if he ever asks you directly what you think or if you notice he starts complaining himself, that's when you speak honestly. Either way, your friend probably already feels the problem himself; most people know when they're with someone toxic, but they need time and support to get out of it, not lectures.
What usually happens is that when you tell a friend something like that, even if you're right, he automatically goes into defensive mode and blames you for not supporting him. A tactic that works better is to invite him to stuff without her in a natural way, without making a big deal out of it - a beer, a meal, whatever - and just be there when he needs you. If at some point he directly asks what you think, that's when you can be honest but gentle, like "I feel like she controls you guys quite a bit" instead of dropping a full-on criticism. In the meantime, don't disappear yourself, because that's probably what he's feeling from his circle while he's in that relationship, and that's what hurts the most.
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