Here's the backstory:

She's a co-worker, she has that princess attitude/outlook but is also surprisingly smart and down-to-earth, and that mix is deadly to me. I love a girl like that. She's also hot, and obviously completely used to getting showered with attention.

Flirting with her was very natural and smooth, and I made myself a challenge by playfully rejecting her advances multiple times. This, I think, made her more and more attracted. Anyway, 2 weeks ago we went out with some common friends, had a few drinks and eventually made out. She was extremely into it.

We've been very busy since then and never really got the chance to meet up outside of work, but continued to flirt on and off.

Last Friday though she had to work overtime. I knew that so I pretended to have some emergency that required me to stay late too. I'm not particularly proud of that, but I had to get her alone and had a few hours to kill. Anyway, once she was done she waited about 20 minutes for me to "finish" my imaginary assignment and go home together, since we live in the same area. All this time I was being very cheeky, push/pulling hard and making all kinds of innuendos. Once we exited the building she immediately started kissing me.

The way home was a combination of make-outs, laughs and an overall great time. However we both had plans that night and nothing more came of it. My weekend was also full since I was away on a ski trip.

Now I don't know what to do. She's 23 and her usual demographic is successful guys in their late 20s / early 30s. She has a rich guy planning to take her to the Tenerife Islands, another wanting to take her to Costa Rica and that's just the ones I know about, meanwhile I barely hit 22 and don't even own a car. All I have to lay on the table is my awesome personality and witty charm. I mean I have my life together, good job and all, but I'm just starting out. I can't compete with those guys on that level.

I have no idea how to pursue this and I'd be lying if I said it didn't scare me, it does. I tried my best to remain non-invested and keep my frame, encouraging her to take those guys on their word and accept their trips. And that's genuine, because why wouldn't she.

Anyway, I can't help but feel the window of opportunity will slowly start to shut if I don't escalate this thing we have between us, but I hesitate.

I need some advice here.

PS: I am gaming a few other girls on the side but I'm not nearly as attracted to them.
PPS: I know it's stupid to shit where you eat. Still, we work in different departments and in this case I've already decided it's worth taking a shot.
PPPS: We're going out with some common friends on Friday night, see how it goes. I should probably attempt a pull since she's leaving on a business trip next week for almost an entire month.

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You can do this! Don't worry about the shit wear you eat thing. Lots of people fall in love at work. You're around people for 8 hours a day and get to know some of them really well. One of my favorite quotes from Silence of the Lambs as creepy as it is, "How do we start to covet?" After Starling gives some wrong answers, Hannibal replies "We covet what we see every day." It is only natural to like people you spend so much time around.

Here is the thing about attraction. Attraction doesn't care about financial status, job security, and all that other stuff. When you are attracted to someone you just like them. I think that is what you have with your co-worker. Granted when it comes to relationships those things help, but they are not what is most important to everyone. There was a homeless guy who had a job doing PUA living out of his van - yes I am serious and he would pull girls from the clubs back to his van. I mean that shit is creepy but he made it work, and you can too for your situation. Some girls fixate on things like jobs, financial status, assets, and all that stuff for sure but she likes you for a reason. You can't go out and change everything today but if you can demonstrate you are working to better yourself what more can she expect of you?

Get your mind right for Friday. You need to be in a good positive frame of mind. Have a self talk if you need to but remind yourself you are a high value guy, you are working to improve your life, and she would be lucky to have you.

Have fun with her and your friends Friday night. Keep in mind she might be a little more shy around common friends so you may need to find a way to isolate. See what you can do before she leaves for her business trip. The logistics of your ski trip and this business trip really hurt the timing of it all but we can't control those things either, so we just have to do what we can with what we have.

I'd seriously consider putting the other girls on hold for now where are others will tell you not to fixate on this one girl and keep going out with them. If she is that "special" to you then she's worth pursuing and the other girls will be there for you later if it doesn't work, and if they decide to bail on you then you can pick up more.

Good luck.

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Been around the world twice, Talked to everyone once...

So you've already been intimate with the girl but you still aren't advancing? I'm not understanding this.

And for one.. Those guys through trips and shit around because thats what they have to offer. Most of them don't necessarily have the boyish fun charm that you possess. I personally don't even buy a girl a slice of pizza unless I'm sure we have a chance at anything. Everything else I bring is a lot more valuable than anything that i can buy so to me it doesn't matter.

I've had chicks of a similar stature that was giving me THEIR money back in my younger "good for nothing" days. While in a similar situation ( guys offering them lavish gifts that they turn down), and they would through this in my face during arguments and you know what I would say? " Go be with them. If those guys are willing to do so much. why are you even with me? " the would usually just shut up after that.

Guys are ALWAYS offering to spend money on attractive chicks; thats nothing new. You just know about the shit outwardly this time around.

You have to believe in your own value dude. Or you may just have to get around a lot more affluent and wealthy guys and see that there isn't anything special about them other than their cash. More money more problems bro; thats a true statement and many times the amount of stress that comes with that level of wealth doesn't allow them to be as cool as someone like you - with less stress.

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I agree, at least bang her a few times.

Hot girls will always have dudes trying to lavish them with gifts because that's all the game they have. And girls will always laugh at and make fun of those guys. What you have to watch out for is the ones that make fun of those guys but still accept their gifts and trip invites.

Yeah I clearly have to isolate her Friday. There will be some other coworkers amongst the people that are coming.

You're completely right on the logistics with these trips though. I'm planing a city break to Copenhagen with a few friends this month, for a couple of days. Invited her and she gladly accepted, then literally moments before we book the flights she receives a mail being told she's going on delegation until April. I couldn't believe my luck.

Anyway, might be a good idea to get some drinks with her tomorrow, escalate a bit and make my life easier on Friday. I'll see if I can make that happen. I doubt she has plans on a Thursday night.

_________________
I know my place. It's me on top of the world.

My in depth texting & dating guide.
There's no such thing as shit-tests.
How to keep a girl.

I know I have to advance. I simply had the worst luck imaginable with logistics. Besides CPH, she also accepted the ski trip invite and eventually had to cancel last second as well, due to external factors we had no control over.
You're 100% right though. The way I worded it made it sound like I'm intimidated by those dudes, I'm not.

Anyway, the reality of it remains that I got fucked over by improper timings, so I gotta make Friday count. I realize that if I don't, there's no way I'm keeping her warm for 3 weeks based on just a couple of makeouts, so it's not like I have anything to lose, right?

_________________
I know my place. It's me on top of the world.

My in depth texting & dating guide.
There's no such thing as shit-tests.
How to keep a girl.

@Update:

A'right, talked to her:

Me: "Did you just have the feedback meeting with the boss? please tell me you got fired. Tired of your ass"
Her: "haha, you wish. Actually got a 2x raise"
Me: "Perfect, you can treat me with some expensive icecream at Marty's tonight"
Me: "Then you're coming with me to buy a present for tomorrow's bday boy"
Her: "I have to go to the mall tonight"
Her: "And I don't really like shopping for gifts"
Her: "But we can go together and we'll figure it out there."

Good enough I guess. We'll see how it goes.

_________________
I know my place. It's me on top of the world.

My in depth texting & dating guide.
There's no such thing as shit-tests.
How to keep a girl.