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Old 06-06-2021, 05:50 AM
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Originally Posted by jespo91 View Post
I have an interesting one going on now, well not exactly going, I am still on the fence about it all.

She is late 20's and I am 20 years her senior. Knew her a little before we worked together. Originally she was hired as my assistant. She spent three years sharing my office, 4 feet from me. She is engaged, has a child. She is absolutely stunning. I cannot say i have run into any woman like her in my life. She is not my assistant anymore but we work closely in the same department.

During all that time in close proximity we got extremely closer. Literally talked about EVERYTHING. Nothing to this day is off limits. We know everything about each other. She knows I look, I do not hide it. Few times the word "Jesus Christ" has come out of my mouth and she just laughs. If she comes in my office and ends up using my computer it is always bend at the waist RIGHT in front of me. No way she is that oblivious about it and she has to realize what is right in front of me. We spend a ton of time together weekly, even in the car visiting clients for day trips. Always just talk. So as the work husband I get to hear it all about home life. Admitted there are at least two, maybe three porn videos of her in existence with different guys that she said she "just was not thinking" and really does not care. College she was banging one of her professors at another professors house for a while. Few other things (she was a wild one) as well as not getting laid at home now. Which blows my mind. We text occasionally, we go out after work once or twice a month, go to lunch a few times a month so she obviously likes my company. If they make a trip to the beach, I will get a bikini pic or two. One vacation they were on i was getting snapchats of the festivities and there were hearts and stuff on them. "You realize what you were sending me with hearts and kisses?"........"Yeah, i was pretty drunk"

But during these conversations she will always throw in stuff. Professor she was banging was waaaay to into her feet she said. "I do not like that, stay away from the feet".....Joked if its doggie and you pull the hair too hard "I will turn around and punch you. You have to be NICE to me". All kinds of stuff like that, details. A female friend of mine said "She is into you. No way a woman is going to tell you all the stuff she does not like if it was not for future reference".......Oh, I never thought of that. "Plus she is comfortable enough to talk to you like that" Interesting. I am not a bad looking guy, I am in shape, I am told I am one of the good guys so i guess it is not too far fetched thinking she may like me a bit more than a coworker? I did joke one time that older guys are better. We know what we are doing and to be blunt we keep our mouths shut. She just chuckled.

There was going to be an overnight work thing her and I were going to to go, that would have been interesting. But due to covid it got cancelled.

I am always on the fence about her. I could push things slowly i guess and see what happens. The old saying that i have lived by forever "you don't shit where you eat" concerning coworkers is off the table with this one for sure.
I've got two things to say about this.

The good one is that, no matter if nothing ever happens, it reads like a friendly and flirty relation, which is a very nice thing.

The bad one is that, if I were you, I would not push it further. In fact, I would not have let it reach even this point. At my workplace, there's a woman who got in one of the top positions by doing almost exactly what you describe. She got (overly) friendly, and flirty, and sexy with an older medium-level manager for quite a while. Then, as soon as he finally made a move on her, the shitstorm started. At the end, she made a deal (I would call it blackmail), and to avoid a very media-public harassment suit the guy was let go and she was offered one of the top-level manager positions in the company. And by the way, she is a rude arrogant person who takes pleasure in gratuitously (and literally) insulting people, and nobody can tell her anything. So, I'm sorry for being the voice of caution, but... well... I'd be very cautious in your position.
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