1v1 is stressful. It isn't fun at first because you don't have a crutch. its all about you vs him and it exposes problems in your game and your flaws very apparently. you'll get your ass handed to you, no doubt. however in my opinion it's the quickest way to get better and improve yourself. It can be fun later though once you start to identify your flaws and improve your game though!
Yeah but that is what ladder is about; you'll always be facing players of similar level. Once you've played enough such that your placement is accurate, I'd think it would still be fun.