I few weeks ago, I drunk chatted my little sister's child hood friend on facebook at 3am. It turned out that she was also dunk, so it went pretty well. The next day we chatted again and she ended up giving me her number and telling me to text her. I have been flirting with her ever since and she seems to be handing out IOIs left and right. Here's how I asked her out:

me- I might be coming into town on Saturday, what are you doing?
her- nothing because i have no life
me- well I'm usually really bored when I go home, so we should hang out
her- ya! i might already be hanging out with your sister anyways.

later on

her- ohh! i work saturday at 4 but i should be done before it closes.. at like 7 or 8
me- sounds good, i will let you know when i know if im coming home or not.
her- alrightttt

The choice I have to make is whether or not to go home. It is a two hour drive and I have no real reason to go home other than to capitalize on her current interest in me. If I dont go, I will be able to party with my friends and hit on other girls. She seemed really into me until I asked her out. I am pretty annoyed that she brought my sister up. Nothing will happen if my sister is there to cock block me, and she knows that. Is this her trying to keep me in the friend zone and avoid me making a move on her?

_________________
if you can't beat them, join them.

No. Here are the two things you said that nuked the interest.

"well I'm usually really bored when I go home, so we should hang out"

Translated into womanese...

Well, hanging out with you wouldn't be great but it would be better than doing nothing. It would be great to have some company while I am bored so how about I bore the shit out of you. Maybe you will even fuck me.

Did you even notice that she went from "nothing I have no life" to "maybe hanging with your sister" right after your comment?

"sounds good, i will let you know when i know if im coming home or not."

I don't want to commit to anything so don't plan on seeing me. Hmmm... If I drive all the way out there then you probably will feel obligated to smash with me. Maybe I might go out there but I am not sure so I will maybe let you know if there might be a chance.

Hence the disinterested response.

Next time try some pizazz!
I will refer to yer as HB 9 year old because it's fucking hilarious and you never said how old your little sister is.

HB9yo Nothing I have no life

You: Damn, I'm not sure if you are ready for it, but it sounds like you could use some excitement in your life.

HB9yo Yes things have been a bit dull lately... blah blah blah blah.

You: Well I am coming in to town around 7 so I'll pick you up at 8 after I check in with my family. I'm thinking ________. Make sure to bring the ruckus...

HB9yo YAY! you are my hero and I think I might want to suck your dick off!!!

_________________
You can't forget about me, stupid. Everywhere I go ima have my own theme music.

gotcha. i dont want to oversell it because my hometown is pretty lame, and i will probably just take her to a movie but i see what you mean. She is definitely still interested, she has been texting me all day, any suggestions of how i could get her to leave my sister out of things?

_________________
if you can't beat them, join them.

Why don't you tell your sister you're taking her friend out that way your sister isn't offended later and knows what's going on. I have a younger sister and I'd feel a bit bad if I was gaming her friends behind her back. I mean you do realize you could potentially fuck up a friendship for her, right?

she's cool with it. this isnt the first time i have hit on this girl. My little sister is avoids hanging out with her. they are childhood friends who dont have anything in common anymore.

_________________
if you can't beat them, join them.

you can interpret her message as if she was inveting herself over ur home, instead of just blowing u away... specially if shes not so friends w ur sister anymore..

But still, what the MPUA said about ur messages totaly makes sense - i only got it when I read his reply

I would go for the 2h drive, it looks like an easy catch! and she can become a fuck buddy in ur boring hometown

_________________
"Fuck it, lets do it"