The mountain creates its own weather system : on the upwind side, moisture laden air rises, cools, and the moisture condenses and falls as rain. So if the mountain is sufficiently large, the downwind side will experience a shortage of rain. (Though a mountain pass may allow moisture-laden air to stream through the gap, making it permanently cloudy, stormy, and not a fun place to cross)
However, if the wind periodically changes direction, then neither side need be a desert(though if one side has ocean and the other has only inland water sources such as rivers, lakes and forest or irrigated land, the latter side will presumably be drier.
So why would the wind direction reverse? Perhaps the daily cycle of sea breezes rushing onshore during sunlit hours, and reversing at night as the land warms and cools more easily isn't a long enough timescale.
Perhaps it's seasonal; the seaward side will maintain relatively even temperatures, while the landward side has hot summers (dry, thanks to predominantly onshore winds) and cool damp winters.
Or perhaps it's unstable, after a few warm days inland, the rising air forms clouds, cutting off the warmth and reversing the prevailing winds until the skies clear again and the cycle repeats. Or probably all of the above in a frustratingly complex and unpredictable pattern...
Perhaps of use : Desert formation. Also note the concept of Desertification which can be a result of human activity.
– StephenG – 2017-11-06T06:35:03.2608I live in a fairly mountainous region of Europe and there are no deserts here. I'm not sure when issues are you having that can't be answered with just "exactly how it is in real world". – Davor – 2017-11-06T13:21:59.263
2There are plenty of mountain ranges worldwide with no nearby deserts. Only in an already dry region or an extremely wide/tall mountain range do you necessarily get deserts. With enough rainfall there is no problem. – Joren – 2017-11-06T13:25:02.857
3I read the title as "dessert" and came prepared for a question on novelizing the Big Rock Candy Mountain. – Bob Tway – 2017-11-06T13:48:09.497
3@MattThrower that sounds like a tasty read. – Paul TIKI -Monica come Home – 2017-11-06T15:08:59.827
2
Relevant: Fantasy Cartography
– TRiG – 2017-11-06T22:26:22.817A single mountain is fine. You need a pretty long mountain range to get the rain shadowing effect that gives you deserts, and even if you do, there's still plenty of situations that give you deserts with tons of water in the air (e.g. Namib - very little rain, heavy fogs) or underground (though you'd be silly to waste it in rain).. – Luaan – 2017-11-07T08:16:38.823