It depends in part on the situation. If you wear a ton of makeup to grab a beer or catch a ballgame, he might wonder why you felt the need to put in all that effort. But if the two of you are dressed up for a fancy dinner, he might think more makeup makes sense. In general, though, most guys don't like it when women look like they painted a brand new face on top of their actual faces. So when in doubt, subtlety is probably best. After all, you want a guy to think you look great, not to think your makeup looks great.