So a bit of back story! Last night I had a couple friends over drinks yada yada typical drunk night. Eventually we decided we need some fresh air so we go out for a walk and as we were walking we pass a group of parents having some beers. Being the friendly overly sociable drunk that I am I jump in the middle of their group of chairs and I'm introducing myself and one of them was sorta a MILF of the street I guess? We share some flirty banter back and forth. It was a good time but then I follow my friends again yada yada 40 minutes later I'm walking back on my own and start talking to them again so they tell me to grab a chair and hand me a beer and we're just hanging out. At the end of 30 or so minutes the MILF says "Well, I'm calling it a night. I'm going to bed" to which my smart ass drunk mind remarks "Alone?" (still not sure if that was a smart move or not) we all laughed, she said yes and that she was too old for me and I headed home.

I'm just looking for a 2nd opinion. Does it sound like she's interested or intrigued enough to leave the option on the table or was it more of an all in good fun / drunk kinda way? She's single, and from what they told me is a swinger too, don't know if there's truth to that though. How should I go about pursuing it from here on out? Since she lives really close to me I figured I could bump into her out front of her house and talk about it, tell her that her age doesn't bother me and that I think that she's an attractive woman and that I am interested, give her my # maybe? so even if she's not interested now, if she ever is she knows how to get a hold of me.

I don't know. Is that too straight forward? Something along the lines of that was my idea. What about you guys?
user
was drunk, met MILF, was super interested, lady is now single, is she interested?
assistant
So a bit of back story! Last night I had a couple friends over drinks yada yada typical drunk night. Eventually we decided we need some fresh air so we go out for a walk and as we were walking we pass a group of parents having some beers. Being the friendly overly sociable drunk that I am I jump in the middle of their group of chairs and I'm introducing myself and one of them was sorta a MILF of the street I guess? We share some flirty banter back and forth. It was a good time but then I follow my friends again yada yada 40 minutes later I'm walking back on my own and start talking to them again so they tell me to grab a chair and hand me a beer and we're just hanging out. At the end of 30 or so minutes the MILF says "Well, I'm calling it a night. I'm going to bed" to which my smart ass drunk mind remarks "Alone?" (still not sure if that was a smart move or not) we all laughed, she said yes and that she was too old for me and I headed home.

I'm just looking for a 2nd opinion. Does it sound like she's interested or intrigued enough to leave the option on the table or was it more of an all in good fun / drunk kinda way? She's single, and from what they told me is a swinger too, don't know if there's truth to that though. How should I go about pursuing it from here on out? Since she lives really close to me I figured I could bump into her out front of her house and talk about it, tell her that her age doesn't bother me and that I think that she's an attractive woman and that I am interested, give her my # maybe? so even if she's not interested now, if she ever is she knows how to get a hold of me.

I don't know. Is that too straight forward? Something along the lines of that was my idea. What about you guys?
user
Met a MILF, she said she wasn't interested, I said that she was and we hung out
assistant