Around 1994 I was trying to make sense of OOP and C++ at the same time, and found myself frustrated, even though I could understand in principle what the value of OOP was. I was so used to being able to mess with the state of any part of the application from other languages (mostly Basic, Assembly, and Pascal-family languages) that it seemed like I was giving up productivity in favor of some academic abstraction. Unfortunately, my first few encounters with OO frameworks like MFC made it easier to hack, but didn't necessarily provide much in the way of enlightenment.
It was only through a combination of persistence, exposure to alternate (non-C++) ways of dealing with objects, and careful analysis of OO code that both 1) worked and 2) read more coherently and intuitively than the equivalent procedural code that I started to really get it. And 15 years later, I'm regularly surprised at new (to me) discoveries of clever, yet impressively simple OO solutions that I can't imagine doing as neatly in a procedural approach.
I've been going through the same set of struggles trying to make sense of the functional programming paradigm over the last couple of years. To paraphrase Paul Graham, when you're looking down the power continuum, you see everything that's missing. When you're looking up the power continuum, you don't see the power, you just see weirdness.
I think, in order to commit to doing something a different way, you have to 1) see someone obviously being more productive with more powerful constructs and 2) suspend disbelief when you find yourself hitting a wall. It probably helps to have a mentor who is at least a tiny bit further along in their understanding of the new paradigm, too.
Barring the gumption required to suspend disbelief, if you want someone to quickly grok the value of an OO model, I think you could do a lot worse than to ask someone to spend a week with the Pragmatic Programmers book on Rails. It unfortunately does leave out a lot of the details of how the magic works, but it's a pretty good introduction to the power of a system of OO abstractions. If, after working through that book, your colleague still doesn't see the value of OO for some reason, he/she may be a hopeless case. But if they're willing to spend a little time working with an approach that has a strongly opinionated OO design that works, and gets them from 0-60 far faster than doing the same thing in a procedural language, there may just be hope. I think that's true even if your work doesn't involve web development.
I'm not so sure that bringing up the "real world" would be as much a selling point as a working framework for writing good apps, because it turns out that, especially in statically typed languages like C# and Java, modeling the real world often requires tortuous abstractions. You can see a concrete example of the difficulty of modeling the real world by looking at thousands of people struggling to model something as ostensibly simple as the geometric abstraction of "shape" (shape, ellipse, circle).