Girl I was dating had a Mom that was a bit too friendly with me, but I just figured she was like that since she was the bubbly type. Didn't help that me and her daughter was arguing damn near everyday over the stupidest of shyt and she had already said she was really happy that her daughter found someone she considered stable and wasn't out doing shyt or not being shyt so she favoured me even though things were falling apart.
We talked alot and at times when I got a bit bold, drank together. I never openly flirted with her and her flirtation with me was more coy than anything, but it was there. After me and her daughter broke up (She broke it off with me to go fukk with this doctor cat who came back home and was "trending") I used to see her and wave/make small talk but never really stuck around enough for a formal conversation until we met by chance a few months later.
I was in the Liquor section buying some Rum and felt somebody knock a shopping basket against my ass like

I look around and she watching me dead in the face talking about "You know I don't drink Rum, I'm a wine woman." I was single, mostly healed emotionally and not to sound crass, still with a semi since it was morning. I turn and tell her. "Nah, you ain't doing no drinking tonite. You put too much salt in ya shyts when you sloshed* A reference from a dinner she had made a while back where she was sipping wine and cooking and ended up oversalting some potatoes and we laughed about hypertension and diabetes and getting older (I was late 20's at the time, she was late 40's) after the dishes were cleared.
We make small talk, dance around the subject of me not being with her daughter and she basically said "Just because you and here are finished, don't mean WE are finished." She didn't ask, she sorta said it, being bold while I was sorta being timid and we played off each other like we usually did when our places were set out, but now that I was single to go along with her always being single (Divorced) we danced around each other for a bit, meeting and mild flirtation out in public until I pretty much told her I'm coming over with not one but TWO bottles of her fave wine and I want us to talk candidly with our shoes off on her porch.
She accepted. I came over with a chiller. We drank, talked, confided each other. I told her about my family problems, why I felt it didn't work out with her daughter, about nearing 30, she talked about nearing 40, her lack of confidence in dating another man right now past just having dalliances, her parents marriage which is still going strong in comparison to hers which lasted a little under a decade amongst other shyt. After we opened the second bottle of wine, I made my move and told her that she has nice feet and I'd like to rub them while she talked.
She looked a bit taken back, but I told her, that if she agrees, go inside, get some more frozen grapes, some sweet smelling lotion come back and put her left foot in my lap.
If she ain't with it or feel like I'm being forward. Go inside, turn the porch light off and I'll leave and we never speak on this shyt again.
She came back in less than a minute with the shyts, I put thumb to arches, oiled up her piggies while she sat there resting on her elbows and we had our first informal date.

One of the best relationships I ever had with a woman, truth be told. Our "Fling" as she called it lasted twice as long as what me and her daughter had. We actually traveled together, did a bit of kinky shyt (Semi-Public fukking) and comforted each other mutually until It ended when she met a dude her age and got married.