How do I go about this?

Hi everyone,

This is my first post, sorry if I don’t format or somehow break a reddit rule! Anyways, I’m a 26 year old male looking to hookup with a friend’s sister who is 41. I’ve met her on a handful of occasions and always thought she was attractive, the last time I saw her she asked for my phone number “Incase I ever breakdown” (we both commuted about 40 minutes to the same city and live in the same town), she was overly nice, recently divorced and generally flirtatious. I tried to flirt back as best as I could but my friend (her brother) who I’ve known since we were 10 was with me the whole time. I never got her alone to talk to her or gave her my number. The last time I saw her was over a year ago, but every time I talk about my family or my friends family I’ll ask “how’s your mom? How’s your dad? How’s your sister?” and he said his sister asks how I’m doing all the time. I learned in conversation recently that she is still single, hasn’t been with anyone since her divorce etc. from my friend. After learning this the desire to sleep with this girl compounded immensely. The big issue now is that I think my friend is onto us, I never get invited around her anymore and I usually get a “she’s doing well” when I ask about her. Now here’s my question; how do I do this without ruining my friendship?

I don’t have his sisters phone number, she’s on Facebook but I’m not. Do I make a Facebook and message her? Do I just knock on her door? I’ve always been pretty in tune with if a woman is trying to get with me, but if I’m wrong I’ll ruin my friendship! What do you all think? Thank you so much!

Submitted November 21, 2019 at 12:12AM

Hi everyone,This is my first post, sorry if I don’t format or somehow break a reddit rule! Anyways, I’m a 26 year old male looking to hookup with a friend’s sister who is 41. I’ve met her on a handful of occasions and always thought she was attractive, the last time I saw her she asked for my phone number “Incase I ever breakdown” (we both commuted about 40 minutes to the same city and live in the same town), she was overly nice, recently divorced and generally flirtatious. I tried to flirt back as best as I could but my friend (her brother) who I’ve known since we were 10 was with me the whole time. I never got her alone to talk to her or gave her my number. The last time I saw her was over a year ago, but every time I talk about my family or my friends family I’ll ask “how’s your mom? How’s your dad? How’s your sister?” and he said his sister asks how I’m doing all the time. I learned in conversation recently that she is still single, hasn’t been with anyone since her divorce etc. from my friend. After learning this the desire to sleep with this girl compounded immensely. The big issue now is that I think my friend is onto us, I never get invited around her anymore and I usually get a “she’s doing well” when I ask about her. Now here’s my question; how do I do this without ruining my friendship?I don’t have his sisters phone number, she’s on Facebook but I’m not. Do I make a Facebook and message her? Do I just knock on her door? I’ve always been pretty in tune with if a woman is trying to get with me, but if I’m wrong I’ll ruin my friendship! What do you all think? Thank you so much!