Hey guys, I’m 31 and the woman is 49.
We know each other from daily life, so there is no “shyness” between us, other than the fact that we “barely talk about what happened when she was drunk”

She is an alcoholic, but she is very strict with herself and only lets loose on weekends or vacation. Her career life is absolutely on point, and she never lets herself have a sip before a shift.

I don’t know the English word, but there is like this cabin/campsite where you can rent a spot of land to plant a cabin for longterm usage. Both of our families have a seperate cabin at that site.

So there were three encounters with us this summer, where we happened to be both there the same weekend (along with family ofcourse)

All three happened at the “almost to the point of passing out drunk” phase of hers. So I cant say with absolute certainty that she is 100% aware of her actions.

All of these conversations happened on the porch of her cabin.

The first time she confessed to me something pretty serious that could ruin her reputation and family. I tried to comfort her, show her I don’t judge her for her actions. Which resaulted in her telling me what an amazing guy I was and any woman would be lucky to have me. Later on it just pretty much turned into compliments. “You are beautiful” “you are great” “you are handsome” i always relayed similar compliments back to her. After that encounter she would always call me “her best friend” in a sort of sarcastic way, making fun of herself, in front of others.

The second time was the first of ‘sexual intentions’ it started out in a very similar fashion, but at this time her 17 year old daughter was also drunk and seemed to be ‘competing’ for my affection. Ofcourse I see her as a child, so I didn’t lead her on or anything. But she would barge in mid-deep conversation a few times. At the last stage of that, I told her about my “last relationship” where my ex pretty much “closed shut” our sexlife. The unexpected comment I got from her then was “oh my, who wouldn’t want to sleep with someone like you” and after a few more sexual remarks, she pulled me up, and wanted to lead me to the backside porch (there is a big party tent there, with a big outdoor couch, and you can seal the tent from inside for ‘privacy’) but as we started to walk, her daughter again, came in. At that point, it was like ‘everything’ she was thinking about/planning to do, just vanished. So the rest of the night, she got really closed off with all the ‘flirts’ and nothing more happened.

The third time was a similar case, but this time after our “deep talk” she would say things like “what if…we could…forget it sorry I’m just drunk and stupid” “maybe we should…nothing, sorry” right before we headed back inside, she stopped me at the door. Laid her hand on my chest and came in for a kiss. There wasn’t any tongue or grabbing or holding or anything. It was just a simple mouth to mouth kiss, lasted about a minute maybe, she had her hand over my heart, and even if it was a very simple kiss, it seemed very passionate.

There was some family commotion later on and she called “Maybe you and me should just move out of here, leave everybody here” ofcourse, she was making some sort lf statement to the family, but i feel it had a ‘double meaning’ I answered back smiling “sure, let’s head to italy” it was sort of cocky and jokingly, but she seemed to have valued that answer more than she let on for the others.

She also has some health problems I won’t get into, but before I was going back to my cabin, she had an episode and her heart stopped, and I was the only one there capable of giving her CPR, and in so, saving her life.

Now, in day to day life, when we meet(never alone) we never talk about any of this, she did come the morning after to give me sincere thanks for saving her life. But other than that, when she’s drunk “we dont talk about what happened” (ofcourse that means everything, she sometimes makes an ass of herself, offends some, says stuff people shouldn’t say etc)

So as I said, I don’t know exactly what she remembers, but the fact that she gets ‘back to where we left off last time’ when we have our talks, then she certainly must know something.

I can’t be blunt with her and just ask straight up, unless I’m 100% sure that she’s of the same mind as me. I don’t know what sort of flirts I can do. I’ve usually been with women around my age, I usually have it going for me that they are ‘impressed’ by me, my responsibilities and humor.

But this is a Woman. Not a ‘girl’, so I don’t want to look childish to her. I don’t know what sort of signs I should look for, what i can say that can easily be ‘excused’ in case she doesn’t appreciate that.

Thanks for reading. Any advice appreciated.

1 comment
  1. wow there are soooo many red flags here

    you say she is very strict, yet she gets terribly drunk on weekends to the point where she does not remember what she does? that is a huuuugeee red flag.

    she makes an ass of herself, offends people, say stuff she shouldn??? OP do you really want to be with a person like this?? its TROUBLE.

    Look, I am almost 46 and to me, a 31 year old guy is either ONS material or FWB material. That’s it. but that’s for me. I mean, you can sleep with her if you want, but clearly this woman is trouble waiting to happen, her being drunk, her health problems, her attitude and a daugher who’s a minor!!!

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