A little, yes. I have to kind of walk next to it instead of right behind it most of the time. But it is way easier than doing the cart-and-stroller thing or trying to chase my two year old through a parking lot, so I'm ok with the slight inconvenience.
I actually paid more attention when I used it for a Sam's Club trip today. If I walk behind the stroller, I make sure one foot is between the wheels of the X-rider and I don't usually kick it, and I alternate between that and walking to the side of it entirely. I am tall, though - 5'9" - so that probably helps.
Re: thecheshirecat, ? for ya