I feel like I am spinning wheels with online dating. I do not have alot of experience and just started researching all this about a year ago. I would not say I have gotten better with women even though I have been reading and researching alot, I would say I am more aware of what to do and the situation I am in. I had recently went on a first date, through text I was trying to flirt and playful and although she was responsive I could tell she was little dull. On the date we met up for 2 drinks on a week day happy hour. I can tell off the bat that the girl was more formal (a career women 26 who lives alone, and likes to live alone she said). I found it very hard to get the conversation to get in anyway playful sexual, although we had great conversations I can tell it was getting to platonic even though in the back of my mine I was trying very hard not to. We parted ways and I texted her next day to let her know I enjoyed the drinks. She said she did not feel a romantic connection. Can somone explain if they have any similar situations and if they can provide insight as to what this means, how would we create a romantic connection in 2 hours when she isn't open to being romantic. We basically matched had a few back and forth texts and met up, so I doubt I came off different from my texts and my photos are pretty up to date. I have had a similar instance about 1 month ago and honestly felt like the same situation and same type of women (career women/non playful/flirty) I am starting to get more experience and could tell through the texts pre date that her interest was enough to go on a date but not excited and on the date I could feel the same vibe.

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You are right I think my main problem is that I try to play it safe and look for a way to get flirtly. I find this is best done as you said being in the moment and the have fun not giving a fuck attitude which will then get her to open up instead of riding on the boring non chemistry building questions. I think this comes from a lack of experience on my part as well as trying to much to not say anything that would stir a negative reaction which may come from an insecurity/lack of confidence. I find myself knowing what to do but not being able to execute and I wonder if that is worse than not knowing this information at all (being that if I was oblivious to what works than I would not be so wrapped up in trying to follow it?)

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I would argue that is worse because in these situations you are basically figuratively castrating yourself. You're not allowing yourself to use what you've learned to actually engage in connection building. So, your first step is to shift your mindset and just free flow. Do what you know is right and feels natural. When talking to an attractive woman, it's only natural for you to feel an intense desire for her. Let that shine through your paraverbals and body language. When you can just be there in the moment, it is EXTREMELY attractive to a woman because you are totally congruent and focused on the interaction at hand. Not reading some mental script that some RSD dope told you to follow, you understand? Also, it is better to stir negative reactions than have a woman be indifferent towards you. Now, don't take that as "okay, i'm gonna go stir negative reactions".. No. In the case of both extremes being indifference or negative emotion, any emotion that polarizes the woman will make you more memorable. But, you should be becoming memorable by showing that you understand her deep desires and wants in life. You absolutely cannot do that if you aren't living in the moment with her.

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