Modern Commentary
Jake is a condescending jerk who's (maybe) better than you at one thing and won't shut up about it.
The older I get, the less I'm convinced that having the skills to back up the attitude is a justifiable thing. People aren't good enough to get away with being toxic. And Jake isn't that good. There's a reason why he's hanging out in a coffeeshop instead of on a job.
He's entirely unqualified to answer any kind of relationship question. I probably should have found a better hook to bring Jake into the comic, at least. Robert really came here to get Jane's opinion on things and couldn't just ignore his old friend/coworker Jake.

Don't be condescending. Whatever you do for a living, you probably interact with folks who know a lot less about that specific thing.
Sometimes, I catch myself doing that and remind myself "Don't be like Jake".- Terrence