There's a lot going on in your post, so I'll off my two cents in pieces.
(09-22-2015 10:55 PM)evilbuttmunch Wrote: Sorry for the long post. Maybe someone will be interested without being too sarcastic.
She is 33, I am 31. I am looking for a quality girlfriend and she fits the mold. She is single for 2 years out of a long term relationship. Since she's older, I am worried that I'm competing with 40 year old men and that she's looking for 'the one' on an online dating site, so no one will be good enough for her
Here's your first problem. I don't know why you're hanging around women your own age for any other than a quick flash in the pan. They've got baby rabies and their looks are starting show the signs of the lack of care their bodies received in their 20s.
You say you use 'hypergamy' to your advantage and then talk about dating girls your own age. Why not date 18-20 year olds? You're only competing with 40 year olds for the 30 years because they can't get the 20 year olds. You're in the sweet spot in terms of age where you can go as low or as high as you want. Unless there's something about your age group or slightly older that you like - you should stop hang out with them.
You're in a good spot to let hypergamy work for you - 20 year olds have a hard time competing with 30 year olds who've got paper and their shit together.
(09-22-2015 10:55 PM)evilbuttmunch Wrote: I have heard that older women in their 30s are easier but maybe not when they are looking for someone to marry within 2 years. I am thinking that my age works against me here.
If you're thinking about a long term girlfriend or more, I recommend going a lot younger. Secondly, just because fatties are easier doesn't mean you send men here advocating you cast your pearls before swine.
(09-22-2015 10:55 PM)evilbuttmunch Wrote: Date 1 (2 hours) is coffee on a Friday night and flirting with some basic kino. I text her on Sunday night and she re-initiates Monday morning and I call her to set up another date for next Friday night.
This a vague description in that you tell me what happened but not really. Like how politicians talk. What do you mean by kino? Did you briefly touch her forearm or was your hand on her waist or better yet her ass at some point?
(09-22-2015 10:55 PM)evilbuttmunch Wrote: Date 2 (3.5 hours) is dinner and bar, and very fucking expensive. She's a half hour late, apologetic, and embarrassed about it, so I know she is into me. She sits with her leg on mine at the bar. We barely touch at the table but after dinner, when we walk down the street I guide her through the crowds by the back. I instinctively offer her a hand for her to help cross a puddle (like I would my mother, lol) and she takes that as a cue to hold hands down the street. After the bar, she drives me back to my car (her idea) and we kiss at a stop light. She stops in the parking lot to let me out but I tell her to park and I initiate a make out session before I leave. It seems like she might be intentionally blocking me from touching her body (it's dark) but I end up rubbing my hand up and down her her leg and she's enthusiastic about the kissing and allows that at least. She texts me when she gets home that she had a good time. I call her Monday night to ask her about how her cat's surgery went (yep) and we set up a date for another Friday night.
My first instinct, without knowing to much about this girl besides her age is to ask why you're taking her out to an expensive dinner? Why not a different date idea like ice skating, a walk in the park, playing pool, or some activity that you enjoy enough that it didn't matter whether or not
you liked her.
Secondly - I don't have a good way to explain it in my head, but try to stop thinking about it in terms her 'allowing' you to do things.
(09-22-2015 10:55 PM)evilbuttmunch Wrote: Date 3 (3 hours),snip
Even if you get performance anxiety - always escalate. If she stops you, take a break and then try again.
(09-22-2015 10:55 PM)evilbuttmunch Wrote: So the mixed signals, I'm worried that I missed my opportunity to escalate earlier in the night, and that I made a complete misstep by escalating too late in the night.
You kissing her and rubbing her up and down in different places but failing to escalate or least try to get your dick, hard or soft, somewhere in and around her vagina probably sent mixed signals to her too.
Girls get confused if a guy doesn't at least try to escalate and look poorly upon men who don't.
Secondly, girls tend to take emotional cues from guys. So if you're stressed during the date it will show and the girl will start to get stressed as well. That combined with lack of escalation are what I think were your two major missteps. Otherwise, you were on track to get the bang if she was willing to be alone with you in your house.
(09-22-2015 10:55 PM)evilbuttmunch Wrote: Snip... One of my problems is that I am an extremely smart and pessimistic person so I can analyze any situation to death and see everything as a bad sign, and I don't have enough dating experience to put any of these things into context.
Right now, I am completely indecisive. Should I simply call her tomorrow to try to make plans for the weekend like I've done in the past or should I ghost and return to contact next week? I am afraid that I came on too strong.
I was like you a lot 8 years ago, a little bit less than that 4 years ago and have some issues with that today from time to time. What issue? Being in your head - having all those possibilities swirl through your mind.
What it sounds like to me is that you need to get more experience with women so that you have a baseline of behavior of girls that you can work with. The more experience, the more you'll be able to gauge body language and whether or not a girl likes you, wants to kiss/fuck you, and how things are going in general. With your over analytical mind, it might take you a while, but you'll get there.
Try not to get yourself financially attached to any woman while you're learning - the price of the lessons you learn can be quite high.
Hope this helps.
G