Well, if you know anyone with a DS be sure to borrow it for a day, and show him games like Nintendogs and Brain Age, Tetris DS, etc. Those kinds of games are actually suited for people who don't like games.
My dad doesn't really like a lot of games, but he plays Mario Kart a little, so maybe give that a try too.
I'd say that your best try would be to get your dad interested in some DS game (it wouldn't matter which one, just so he likes it) so he will want to buy it. Or you can tell him how boring the car is, and how it's very good for trips, etc. Every summer I go to my Grandma and Grandpas house (which is 12 hours away) and I'm not sure how I'd survive the trip there without a DS, or some gaming handheld.
Also if the price is a factor, start out with an older Nintendo console (such as a GBA) and work your way up from there. It's always good to start out simple with parents because somehow, I don't think I'd own a DS today had I not slowly and carefully tried to get the newest console. See parents don't like the idea of "my kid is wasting hundreds of dollars on all the newest consoles that are going to get old anyway" so that could be a factor itself. So it's best to buy older things, and gradually ask for the new stuff, that way your dad gets more used to it.
I'm a bit of an expert in the ways of how parents feel about letting their children buy consoles, etc, so let me know if none of this does any good, and I'll continue thinking.
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