First of all, you should never ever wear shorts that look like you got them from the kids section. You might think it looks sexy, but trust me, it doesn’t. If your hoo-ha is showing through your shorts and your butt cheeks are showing through, I think it’s time to throw those shorts out. Most guys when they see girls wearing shorts like that, it just makes them look trashy and overall gross. Plus if it’s too small, it’s not going to flatter your waist or back side. Find a nice pair of appropriate shorts to wear on a nice date.