Summary:
Very weird and fun night that completely blew up on me. Friday night, I was out with this girl at a bar when she invites me to a strip club. We go to the club and everything is perfect. We are going at it hard at the table with the stripper giving me dances while I made out with the girl I came with. Everything heats up to a boiling point. We are going to go upstairs for privacy so I go to the bathroom and when I come out the girl is gone. Boom – just disappears. I don’t hear from her until the next morning when she texts me that she is sorry and that she just freaked out with what was about to happen.

This whole situation I messed up from the start but the ending was hilariously bad.

Details:
I met this girl 5 months ago on a business lunch. She was a vendor trying to get in the door at our company and my boss asked me to go lunch with her in his place. Since he didn’t want to go it meant she had zero chance of getting in and my job was to blow her off. I hate these lunches and my goal was to get in and out as quickly as possible. However, when I arrived I was pleasantly surprised and I found this girl to be both beautiful and with a great personality. We clicked immediately and we had a wonderful lunch that lasted awhile. So, I decided to help her get into our company. She was young (28) and talented and needed a break. Although my attraction to her had to have factored into my desire to help her is wasn’t the main reason and I had no intention of gaming her. I really just wanted to do something nice for her. I didn’t think I would likely ever see her again. So, over the next month or so I tried to help her set up some contacts when luckily an opportunity arrived for me to use her on one of my projects. We worked the deal over a couple of months and in mid-November we closed a minor deal. Okay, great. I felt really good that I was able to help her. I didn't think past that.

However, I get an invite from her to go to this super trendy restaurant to celebrate. Now, things change for me and I am interested in her or at least interested in gaming her. I am not sure of the context under which we are going out – client/vendor, friends, more. I decided it didn’t really matter since I will be with her and since my game is usually solid that it gave me a shot. So, I start gaming her and building comfort and attraction. I am mixing natural conversation with routines and dhvs and my game is super tight the entire time and the evening is awesome and we are there for 5 hours. However, I can’t get myself to escalate touch and I am frozen. Two things are freezing me: 1) I spent a tremendous amount of time helping her out of kindness. If I really start gaming her now it just destroys that help because then it just became a big plot to get her and 2) I am 45 and she is 28. Despite the signals she was giving me I was really afraid she would reject me and that I would go from helpful to creepy. I was too invested in her. I was really upset with myself because I don’t normally freeze up like this. The dinner ends, I hug her, and I get home at 12:30. At 1:00am she starts texting me and flirting and saying she is laying in bed and we should have hit the bar after and blah blah. This means I had an opportunity to bounce her somewhere else and to do a lot more. Big fail on my part.

Yet, I am still a loser and I still can’t escalate. I normally escalate quickly and if I get blown out I get blown out. No big deal. But this was a super big deal to me. She starts texting me the next day and the clear play is to take her out again. But, I can’t get myself to do it. She stops texting me the obviously day – obviously because I am being pathetic. I let it go since I was traveling out of the country the following week. On my trip I am with a bunch of different girls and I have zero problems escalating and I feel normal again. However, while I am on the trip I am texting with this girl back home because there were problems with her deal that needed fixing. But, the reality is that I also really liked texting with her. We clicked.

A couple more weeks pass and then last week this girl closes a very big deal with our company. I have helped her career tremendously by getting her in the door and I am very glad for that. I assume that is the end of things between us and I feel very good that I helped her. I liked being the guy that she someday with say, “I remember this awesome guy who once helped me……” People have helped me in such ways in my career and I liked repaying that kindness. But, I get a text from her saying simply “we should go out for drinks at xxxx”. I feel really stupid that she has to be the one that asks. I say yes and I recommend Friday night. She accepts.

We go out Friday to this incredibly trendy and romantic bar and we hit it off as always. I finally tell her that I am attracted to her but I am torn because I really just wanted to help her and it wasn’t some plot to get her. She says she never felt that it was and that she likes me too. Everything is cool – except I can’t get myself to touch her. It is driving me nuts. I have kiss closed girls in under a minute and here I am with her telling me she likes me and I still am frozen. I don’t know why really because the path is obvious. She gets a text from a stripper friend and this friend invites us to this high-end strip club. We go to the club and get a table up front. Everything is awesome and her friend is over playing with us. The two girls are kissing and I can’t believe my luck - except I still can’t get myself to touch or kiss her. I have completely psyched myself out.

We are outside on the patio taking a quick break and out of desperation I said to her, “I know what to do. I am just having a problem being that guy given our relationship and how you know me. Do you want me to switch into that mode?” She replies yes and that was all it took. I go into auto-pilot and I kiss her and I escalate quickly. Soon we are making out at the table and she is being super aggressive too – she is biting my neck and grabbing my junk and my hands are climbing up her dress. The girls are making out and I am getting lap dances and I am living a fantasy. The stripper recommends we go upstairs and do whatever we want because we are about to get in trouble. I go to the bathroom and I come back and the girl is gone. She just fled. Massive fail. lol.

I sent the girl a message just saying, “that’s cool. Just let me know you are okay”. I am worried because I don’t 100% know that nothing bad happened because there were no hints of an issue. I thought of calling the police. But since her coat was gone and she seemed like the kind of girl who would flee I figured she left on her own. She texts me the next morning and apologizes and says she freaked out because of what was about to happen. I am not sure how to play it. I like her and wanted to see her again but if I never see her again in that context it is okay. I was really more concerned about just playing it right, although I have messed up so much by this point it doesn’t really matter. I tell her not to worry about it. Then the following exchange takes place.

Girl: I am not sure where to take our relationship at this point. I really think you are an amazing person.
{I think she is either blowing me off or she is unsure of what to do and is looking for some leadership from me. Either way, I figure being a bit aggressive is the best play}
Me: I am not sure either but I would kill to take you to xxx as either friends or with whatever thing we have going on at the moment.
Girl: I would love that.
Me: Do you need time? Otherwise I am taking you next Saturday.
No response for 3 days.

I am really surprised I didn’t hear back from her. Normally, I wouldn’t have said, “do you need time?” but with our professional relationship I wanted to give her an out so it is not awkward. I assume if she didn’t want to go she had a great out and would have simply said, “I need time” and that would be the end of everything. My best guess is that she blew me off and there is nothing more to think about. My play now is simply to move on.

Anyway, fun situation that I messed up terribly.