Let me start off by briefly describing three different nights on the course of around 5 months:

1. Meet chick through a friend while we were going out clubbing, made a real good first impression, was able to make out with her in record time. We had fun all night drinking, I got her number and through text she told me she wanted to go out again. Long story short, I began texting her (this time with no alcohol in my system and a bit more consciousness on the things I like to talk about), I demonstrated value with the activities I do but the initial attraction slowly faded and she eventually stopped texting back, unable to go out again. I saw her again at the same club a few weeks after and she was a avoiding me, even though I never pushed on it when we stopped talking.

2. Was out with my brother watching live music when one of his friends brought some chicks over to the bar, they are all around 5 years older than me but one of them was around my age (a bit younger). We hit it off that night, I have no problem talking to girls in the moment, I'm humorous and I display value in my own ways as a bit more mature guy for my age. We kissed that night (we were a bit drunk), but we were talking about shit we both really liked. I got her number, texted her the next day so we could go to a club, she just said "I can't :(". A few days later my brother's friend was telling me why I hadn't gone out with her again, that when she was in the car that night on the way home she was talking about how much she liked me and that they should let her know when I was going to be at another gathering so she could go. I began texting her a bit more after that but it was nearly impossible for me to reconnect the emotion we felt that night. I feel like I can't text them unless I have a plan for us to hang out, and it has to be in group because or else it might be awkward if it a second date alone and the first time we were kind of drunk.

3. It was a Friday, I had not had contact with the last girl for weeks because I really didn't know how to reconnect, was feeling pretty damn shitty about myself that day. My brother convinced me to go to a birthday party at a club, while we were there, there wasn't really any girl I could hit on. All too older and the others I already knew as close friends which had boyfriends. My brother was waiting on a girl to come to the club and with her she brought two other friends. One of them was reallyy hot, with the self confidence I had that day I quickly decided she was way out of my league and I was not going to get rejected once more and have my confidence come to an all time low. I was having fun by myself that night, just being friendly with all of them, I had a drink, which the hot girl took some from me (at this point I was a bit drunk and realized right there how hot girls can always get what they want). At that point I began to tease her a bit about it, like "hey you just took half my drink without even asking, haha what's up with that", we laughed, she said you look like a "nice person", she began dancing with some dudes from the other table, they offered her a couple of drinks which surprisingly she came back and shared with me. At this point I didn't really care what happened, I began dancing a bit with her but didn't actually think I was going to get with her, she turned around and told me "hey, I'm going to give you my number.." she said something else which I don't remember cause I stopped her and pretty much just kiss closed her right there on the spot, which gets me thinking about "I have no clue if she was unaware I was just going to go for it given that I hadn't thrown her any moves that night (although she initiated tongue kissing)". Anyway I drove all of us in my car to where their car was, while we were walking out of the club was when she asked my name and I had just overheard hers a few seconds ago. I texted her my name just in case she forgot and a few minutes after she said "Thank you I had a great night :)" "Drive safe". After that night I thought, hey I was just lucky this night, I shouldn't hold myself to her, just think it was a good experience and if I text her and things don't happen I won't feel bad because things just might have been going on in the moment and she is at another league and on top she is a few years older than me. Learning from the experience from the last girl, I began texting her 2 days later much better, I had a great plan to go to a pool party but she had gone on a boat the day before and was exhausted from the sun. She at some points in the conversation commented that we lived close and there was no reason not for us to hang out soon. I just felt it would be awkward for her if at that instant I asked her out on a date alone and waited for the weekend to go out in a group again, unfortunately it was not possible and she left a few days later on a summer trip for a couple of months, I didn't want to end our conversation like "well so I'll wait for you to get back" so we stopped talking a few days before she left given that it was gonna be impossible for us to see each other before she left as the weekend had already passed.
I never let her finish that sentence after "hey, I'm going to give you my number..". and I don't know if she wasn't 100% comfortable with me kissing her even if she kissed back with tongue. Although, she did throw some comments that indicated interest, more than normal.

Final thoughts and questions:
Even though I am a much more mature guy for my age in a lot of stuff, she is still older than me, has gone out with much more experienced guys and I would have to be in my comfort zone in order for me to show her value (not at a club). Even though she doesn't know I might be younger than her (2 years maybe).
Why did she give me her number? Is it bad that she was the one with the initiative?
When she comes back, should I give her a phone call and try to connect with her maybe by bringing up some stuff we talked about in the car and then ask her when she is free?

With these three girls, we've have had wonderful nights, it has just been impossible for me to get a second date with them.
One problem I encounter is that I don't have a lot of friends I can count with (only one friend and my brother with his group of friends) and it is hard for me to come up with plans to go out, so I can't just be texting them and never tell come up with a going out plan. I have good ideas for alone dates but it would make it awkward if I can't get them comfortable in the texting game and I just throw that out there.

I obviously want to go out with either of the last two chicks because they are still in a decent time frame, but I'm not stuck on them specifically. I have learned that there are a lot of chicks and that I'll live for the next one if this one doesn't work out. My goal is to pass this Sticking Point of not being able to see them again after a good night. I also have been doing some reading on this blog and I noticed a comment of someone saying "making out with a girl on the first night increases their flakiness". What do you guys think? Might they think "well just another crazy night and put it under the rug?"

I know I just wrote a bible but I would really appreciate it if you guys take these stories apart and let be know of my blind spots so I can begin working on building confidence in this area in order to get over it!

Thanks again

It seems like your game is pretty solid in person. Being honest, I didn't read it all. What I did notice, however, is that your interactions fizzle out over text. I'm going to propose two options for you. 1) stop texting, and call them. 2) Text less.

I've found since I stopped texting girls, and I call them, my success rate has skyrocketed. Next time you want to text a girl, just call her instead. Ask her if she has time to talk, bullshit about how awesome your day was, and take it from there. I find that when I do this, I can set up dates really easily. Sometimes I call a girl with out even planning to set up a date, and the conversation just goes so smoothly that I have a date when I get off the phone.


Try it.