My sister’s best friend has had a crush on me for years but she was too young and then I got in a LTR. My LTR recently ended.

She texted me one night a few weeks ago to see what I was doing. She didn't say it overtly but I could tell that she wanted some action.

I needed to be up early the next day so I declined and we planned on meeting for drinks the following night.

The following night she was out having dinner with someone else and I sensed a flake coming so I preemptively asked her to reschedule for later in the week.

She agreed but then canceled the day of our meeting later in the week with a BS excuse. I reacted with a slightly negative text, “Boooooooooo” which was a mistake.

Since then I texted her several times (she didn’t return most of them) and I think I came off as needy. She invited me to a party she had but she waited until the day of the party to invite me (I think to test my neediness). I didn't go because I didn't want to appear needy.

We hung out a few times (with other people) when my sister was in town over Thanksgiving. I can tell she is still “kind of” interested in me, but she is not a young girl with a huge crush on me anymore. She is now a beautiful woman with lots of options. Anyway, I expect her to invite me to hang out with her (in some capacity) soon, as long as I don't text or call her again in the mean time (that would probably make me look needy at this point).

My plan is to initially decline her invitation so that I don't appear needy.
Then, the next day I will text her saying, “you impressed me a few weeks ago”.
She will text me back asking how she impressed me.
I will finally get direct with her (after all these years) and say, “it took some balls to cancel on your dream guy … but why should I give you another shot?”

I'm thinking this approach will put me back in the driver’s seat and make her qualify herself to me. Do you guys agree or have any better ideas? I intend for my texts to be flirtatious but could they possibly embarrass her (by calling her out on the fact that she's had a crush on me for years)? Also, how should I pursue her if she doesn't contact me like I expect her to?

it's good that you realize that the text you sent "Boooo" was a bad idea.

i'm not totally convinced that the "it took some balls....." text is a good idea...it let's her know that you're still thinking about the fact that she flaked on you.

instead, what i would do is 1 of 2 things.

A) agree to hang out with her when she asks, and then flake on her as payback (mean, perhaps, but payback is a bitch)
B) don't agree to hang out with her. tell her you have plans with someone, but leave it very vague...if you leave it vague, she'll eventually talk to you again and soon inquire with whom you were hanging out with and what you were doing with that person. (date, basketball game, etc...etc....)

you can make up your own story with whatever suits you.

I already went with option B when she invited me to that party and I didn't show up. Later she asked me why I didn't show. I was vague and just said I was out late that night.

Where do I go from here? Wait for her to contact me? Contact her?

If I had a chance of seeing her and running game on her and not seeing her I would choose the first option.

Why get involved in her game? It doesn't achieve anything. You can't seduce someone you're not in contact with. Can you?

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This, dont flake on her just yet, maybe AFTER you guys hooked up that you can play it cool. You could have gone to her party and flirted with her friends if she was too busy for you there and get her a little jealous, it was a mistake not going there. Next time she wants to hook up, go for it, and game her.

Given everything that's happened to this point, should I wait for her to contact me or should I pursue her?

do a little of both, go do something (like a concert she'll like or whatever, a movie etc) and text her that you're going anyway and that she should join you

That makes sense, thanks man.

no problem bro let us know how it went!

Tonight I texted her around 9:30 letting her know I was out at the bars with some of my friends and said that she should come down (she's very social). She never responded to the text.

Do you guys think she's playing hard to get or do you think she just doesn't like me anymore?

I'm sure she'll text me tomorrow with some excuse and I'll be like don't sweat it. Any ideas on what else I can add to the text to create some sexual intrigue/get her thinking about me?

This is the point I was making. Now you're playing HER game of cat and mouse.

Had you just gone to her party and ran tight game on her you'd have her eating out of your palms.

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*Justice renders the WEAK his due*
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Tweeby is right. To be honest you should let go...at least dont ask her out anymore or text her. Go pick up other women..could get her jealous. If she really wants to go out with you she will work for it but it doesnt seem like it to me so you should move on.

On to the next one. you came off as needy and you tried to beat her at her own game. bad move. your big mistake was missing out on the party. Jealousy sets work wonders when it comes to gaming chicks. this is all part of calibrating your game just learn from it and move on. your showing to much interest in the girl, your with your buddies at the bar why is this bitch on your mind when there should be other girls at the bar for you to talk to?

i think the roles are reversed and you got the crush on this chick.

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Yippi ki ya yippi yi yi yo, if you can't swim don't smoke my hydro.

You're right, the roles are reversed, shit!

I was just following Chillburg's advice last night which seemed like a good idea. Did I not follow it corectly?

You did the right thing, she is just a lost cause and sending her that text was good because now you know for sure she's gone.