Sorry for the long cringe post. Really appreciate all the help and advice from folks in this group 🙂 (Previously posted in fb group, need advice from you guys and Alex.)
Context:
Goal: My goal this time to be honest was just to kiss a girl.
I need to learn:
- When escalation failed the second time, was it because I think I made kiss a big deal.
- I have fucking weird body language, I think too much, I don’t know how kiss or foreplay with a girl.
- I want to avoid kissing at all. I don’t know how to do it, or how to learn it.

General feeling: I felt really bad for this girl.
Girl: Like a 9, perfect figure about 5’8. Matched with her on a league app.
Me: I lost about 20 pounds in last 2-3 months and 4-5% body fat. I look much better in person than in my old pics.
Time of duration: 2-3 hrs.

Questions:
- How can I work on the kiss thing? Is it required?
- When she is grinding on me, what should I have done? Can I take off her clothes? Should I touch her at other places on the body?

Initial Meeting:
I reach her building, text her. She comes down and brings wine glasses. I make jokes, she laughs, it’s vibing.
Rooftop:
She takes me to the rooftop, a nice view of SF. We are alone there. She sits on the couch, I sit next to her. We start drinking wine. (I had a mishap with opening the bottle, she helped me.)
We are close but not touching each other. We just talk about general stuff, I maintain strong eye contact, hers is on and off at times.
I say some observations, just funny comments on what she says, she laughs often, and there are some silences in conversation but overall I feel it’s flowing.

Rooftop to Apartment:
I make comments on how a bed is important to get in her new apartment. She laughs. From what I remember, she got up and said you passed the serial killer, let’s move to the apartment. I make some comments in the lift. It’s vibing great.

In Apartment:
Normal conversation/ Building connection:
She sits on the couch, we’re closer now. I am trying to build a connection right now. I ask about her school life, college life, her job. I try to do cold-reads, honestly not that good. But I make some funny comments, she laughs often. There are some lulls also. At times, boring topics.

Escalation(sequence may be jumbled):
Aim: I want to verbally escalate.

Initial

I make a comment saying she is cute based on something with the furniture and then I follow with funny comments.
I hold her hand, touch her ring, then pedant on the neck, make some comments.
She never hesitated with my touch.

Hair

I caress her hair, make comments on her appearance now. She is pretty close to me. Happens for a few mins.
Maybe do a few high-fives.

Thighs

I touch her inner thighs, she seems unfazed. I say you should wear yoga pants instead of jeans(she said something before about some yoga). She says “what are we going to do about it?”
It was too sexual for me, I brush it off. I don’t know what to say.

Face

I start touching her face, then her lips, and her teeth also. I explain the features of her face while doing this.
I also comment that she has very kissable lips. She asks why, so I elucidate more things about her lips.
I make some excuse in conversation to hug her as well.

Thighs again

We’re quite close, I touch her thighs again, I make some comments on it again. She tries to be logical at times, and I say some stupid things.
She says you are distracted. I replied yes. We come quite close.

Hand

She is breathing heavy. I have no clue what I am talking about now, but I am talking slow. She is too very slow in speech too. We do this for 1-2 minutes.
She touches my hand, we touch for some time.
I think she tried to touch my thighs also, I don’t remember for sure.
We’re quite close at this time, with very strong eye contact. This built some sexual tension. She could hold it, she never broke it.

Before kiss

I might have played with her hand, face, thigh in between again.
We are face to face close now, I say I want to do some naughty things with her lips.
She says you are distracted, I mention some other things.
She keeps looking at my lips, we are so close I go for the kiss.

Fuck up Begins
Kiss(Where I fucked up first)

I have never kissed a girl before. I just suck on the lower lip and pull back. I honestly, didn’t know what to do at this point.
I thought she would also do something.

Aftermath of horrible kiss

We talk for 1 minute, she moves further away, becomes very not interested in the conversation.
She says “You had your chance to kiss me, and this is what you did.”
I am like do you want to practice? She looks at me weird.
So I start analyzing it, was it bad timing? She is like “no it was the correct time, there was no chemistry, I didn’t feel anything.”
I try to understand saying, ok why.
She says, you are being weird, I haven’t analyzed a kiss like this before.
I try to justify saying I had a long day and haven’t been in a relationship for some time.
I try to salvage it, I become needy I think. Honestly, she didn’t respond much to anything after this.
I tried to build a connection again.
But she is like why are we still talking, why are you asking me questions.

Trying to leave

I feel she wants to end it but won’t say it. We talk weird for a few mins. On and off, I can’t bring it back honestly anymore.
She says I am a nice guy and something along those lines.
I say to her, ok I will leave now. I want to go to the washroom.
I ask her where it is, she is like find it yourself. She is pretty pissed.
I come back.
I say it is ok, let’s just finish the wine, I will leave and I had a good time.
I felt really bad for her, and just tried to make her more comfortable at this point.

She drops the wine on me

She spills the wine on my thigh and her sofa. I didn’t like this at first. But I say something funny about it, she laughs.
She takes off her jacket.
She brings a towel starts cleaning the sofa like crazy for 1 min. I kinda a bit pissed, I say my pants are dirty too!

Cleaning my pants

She starts cleaning my pants. She comes super close to me. She starts breathing quite heavy. This happens very quickly. I was taken aback, I thought it was over.
She stands up. I wrap my hands around her neck.
I say we should kiss again. (But I am not confident about kissing atm). She says you shouldn’t say that just kiss.(err...)

Cuddling

She says we should cuddle. She practically pushes me to the couch. She cuddles with me for like a few secs, she says you’re too stiff.
I say ok, let me take my jacket off.

Grinding

I take my jacket off, she jumps on me and starts grinding. Like really hard.
I wasn't honestly ready for this.
I can’t get hard at this point for some reason. Anyways, I kiss her neck and ears, she doesn’t let me kiss her lips again.
My kisses are weird I think so.

End to grinding

She moves her head up, she says like what?
I say sorry I can’t get hard at this point.
She says that not the point. You are too in your head, you are very protective/stiff.
Give her some other bullshit reasons, she doesn't buy anything. She says it doesn't make sense, you are too stiff.

End

I tell her I am sorry and not that experienced, some past stuff. (I didn't feel confident to tell her I have no experience.) Anyways, just caress her arm, relax her, and make her feel comfortable. Talk about random stuff.
Then she says we don’t have chemistry, I agree. I just say I am leaving, I collect my stuff, hug her, and leave.