I’m shy, how do I ask girls out?

I am a fairly shy person until I get to know someone and by that time I am always labelled as the "friend." What is a good way to ask someone out when you don't do well just going up to someone and straight up asking them out because you are too shy etc? The main issue I have is that I have been cheated on in the past and I know I am not the thinnest guy out there plus my interests lie in books like Necromancer so it's really hard to find someone that goes alone those lines too and when I do I always get stuck in the friend zone. - Billy from Chicago, IL

HAHA! Love the Neuromancer reference. Sounds like Dr. Barbarella is your girl! But now, let’s talk about this issue of yours.

I will in no way, EVER label myself a pickup artist. I don’t know how to pick up girls, but what I do know is how to talk to people, and THAT is what you need to focus on. Keep in mind what it’s like to be on the opposite end of things. To be the girl getting approached by a guy, or creepily hit on. And remember, girls get hit on by creep-jobs all the damn time.

The creepier the guy, for some reason, the more confidence he has. Sometimes it works for him, most times it doesn’t, but it’s still that confidence that girls are attracted to. So number 1, confidence! You’re not the thinnest guy, who gives a shit! Lucky for you, girls aren’t attracted to guys based on physical appearance alone. I mean, don’t get me wrong, getting into the gym and taking some ownership for your appearance wouldn’t hurt! (This coming from the guy who weighed 215lbs about a year and a half ago.) But that’s not everything.

Second, don’t ask them out. It sounds weird to be like, “hey, would you want to go out sometime?” The timing needs to be right, you’re lacking in confidence by asking and just sounds weak and frail. Stop focusing on “asking” them out, and just focus on talking to them. You get stuck in the friend zone? Cool! This isn’t always a bad thing.

My guess is you’re a little younger if this is happening. As you get older, the “friend zone” thing stops happening and you just say %&$# it, I don’t need this broad in my life. Alright, maybe you don’t say “broad”, but I do. Regardless, USE the friend zone. Ask her about it. What she looks for in guys, how different guys approach her. Use it more as a learning experience than anything else.

Overall, stop “asking them out”. Talk with them. Flirt. Speak your mind. Compliment the girl. OR, tell her the truth. If her makeup looks weird, tell her she’s gonna have a hard time picking up a dude wearing blue eyeshadow on her super pale skin with bright red lipstick. Tell her she looks like an all American hooker and you don’t know whether to give her money or get her help. On second thought, maybe NOT that, actually. Yeah, don’t go with that.

But talk. You’ve got time, there’s no big rush. And you don’t always need to talk to the pretty girls, talk to whoever. Get some practice, so when the pretty ones come around you’re not stumbling over yourself. Practice. Talk to random people at the grocery store, in line at Target or waitresses. Waitresses could be your best practice. They HAVE to talk to you. Just, don’t creep ’em out. Keep it cool, keep it casual.