I was asked out for a few drinks (day date) by a very successful, attractive woman. She's actually my realtor who've I've only physically met while looking at a potential lease property and interacted with no more than 15-20 minutes.

To be straight forward, she needs nothing from me. She is in her late 30's/early 40's(?) and is only doing realty as a part time hobby. She is loaded with cash, will go to another country just to try a new food for the food club she created and is known for being caught with a celebrity from time to time. Financially, I have nothing to offer her. So, I won't presume that is she has shown any interest. I don't imagine her to be the type to be on the prowl for a lay. At the very least I want to present myself as someone she'd like to see again.

So, how should I carry myself? Should I be sexually aggressive? The thought of that gives me the same anxiety cold approaches do and I would hate to catch myself being awkward because I am uncomfortable testing those waters.

EDIT: Details.

Field Report

First of all, thanks to all of you for being honest and constructive. Somewhat regretfully, I didn't have time to see all of the suggestions you guys responded with. I couldn't choose which one of you I wanted to reply to first. So, I'll just do a follow-up here.

We met at a brewery/restaurant and since it was a nice day outside I found us a table on the patio. It's funny that Make3said that I was the girl in the situation because she actually gave me a false time restraint. Maybe that was a result of me making it clear that I hadn't sat around all day waiting for this date (I hadn't) and had actually been quite active around town doing relevant "alpha shit". She said she could only stick around for about 30 minutes.

Five hours later and everything was going great. We'd both loosened up from the drinks (didn't get drunk, mind you) and I managed to keep a smile on her face. I watched my posture, smiled a lot (which surprisingly comes naturally when one is having a good time. Who knew?), found commonalities and use those commonalities in conversation to find even more commonalities, asked her about her projects and goals, which gave me the opportunity to talk about my own.

I think she confused my kino anxiety for non-neediness and initiated it herself. Though I still think it was bitchy on my part to not initiate the kino, I mostly blame that on the way we were sitting. I had a chair next to hers, but there was a little bit of distance in between us with me leaning back and, AT THE TIME, felt it would be too awkward for me to lean in just for that touch. Physical contact is crucial, BearPaw_LikeAnIndian. Her kino consisted of leg touching, arm touching, hand touching, and whatever other contact she could get by with. If five hours of sitting with me on our second meeting wasn't enough of an IOI, she touched her hair, continued the conversations, laughed, made eye contact, etc...

I think the cherry on top, for her was, my non-reactiveness and non-neediness. She'd talk about her international romances, an ex-boyfriend, or her interactions with Sandra Bullock and Matthew McConaughey as I would carry on as if it were just as common for me to do the same daily. I didn't mislead her, I was very charismatic.

How it ended may be considered a let down for most of you (I for one have pride in the communities somewhat high standards and constant discontentment). For all of you who suggested that I be sexual, it didn't happen. I had a fear that it would create an awkwardness about me that she would have noticed and, poof, there would go the charisma. I know without a doubt had I had the proper escalation game, I would have woke up at her house this morning, instead of... well, that's left for SedditIfICanDoItYouCanDoIt. So, my close was, she begged for a hug and was suggestive of wanting more, so she got half of what she wanted and the other half she settled for inviting me out tonight to meet with some of her inner circle and include me in a few plans they have for the evening... some kind of wine tasting and some other deal that she recommended me pass out business cards and talk about a few of my ideas and projects I have going on.

So, The Close: second date and the opportunity to be introduced to a somewhat exclusive "inner circle".

I imagine if I carry myself the same way I did yesterday, I'll maintain the friendship but be permanently placed in that friend-zone. So, I'll see what I can figure out about escalating this to the next level and use tonight to show that I am not intimidated by her circle of friends, whom I assume will be cocky fucking businessmen. I think that will possibly make it even easier to take this to the final destination of seduction... well, one of them.

tl;dr Met up with chick. She gave me a 30 minute false time restraint. Five hours later, I successfully became someone she enjoyed being around yet failed to escalate sexually. She decided to include me in some prearrange plans she had with her friends tonight. Confidence Close

Note: Too long; Didn't proof read.