Custom maid 3D-2 has a lot of features for all sorts of public's. Depraved ones, weebs ones and even for rpg enthusiasts It's pricy though and the translation isn't that good, mostly machine made There's other games out there but those are for more niche audiences

It will sound corny and cliche, but be yourself ^_^. Being friends with a guy is the best first step since a boyfriend is a friend! Approaching can be really hard (I'm super duper shy too x_x), but sometimes it can just flow naturally. Just be yourself and give it your best shot!