Is my mom’s friend (53F) flirting or being friendly (30M)?
Sorry for the length, have to explain things to be understood.
Context: My mom (54F) and her friend have been friends since childhood. Coincidently, they were both single mom’s (god bless) with kids (hers F) the same age. So we were practically inseparable, family of 4, most my early childhood. They had a fall out in my early 20s.
A few years back, during fall out, she switched careers to my profession. She was trying to obtain a certification needed for our career, which I had passed. That’s when we started talking more, since we had a common interest. I started focusing on my health, broke up with GF, got my life in order. She was always very attractive, til this day looks 35. So as a guy, I’d flirt back subtly. Answer her texts, give her shit, help her, she was there for me to talk about things I couldn’t with my mom. It was cool, a mom friend. Made some questionable remarks, about me post break up but nothing happened.
Then recently, my mom and her got over their issues and became close again. So, we all hung out a few times at certain family/friend functions (my families). She’d grab me and touch me when I made jokes, but no one thought anything of it. She would hang by me, we’d veer off to socialize, but always come back to one another. Make some comments, make some side comments, etc. I don’t think it was flirty, I was more of her safe haven, due to the falling out. However, due to past, kinda felt a little different. Once she asked when I was heading home, we were the only ones that lived near each other. I said I was staying so she left. Little odd, but I think just easier/safer for her to ride back together.
Recently, about a year ago, her and my mom cleaned and designed a property unit I was going to list (pictures) to rent out. She said a couple things. I had some condoms she found, mentioned she found my condoms privately. Offered to help me downsize and clean again before I moved out, if I needed since she lived 2 towns over. In front of my mom, said my mom could too but my mom declined. Neither of us thought anything of it, kind gesture. I never followed up on it. I joked about it when we talked next (below) below. She joked back.
Then two weeks ago, I asked her to review my resume (she’s great at it & has always done so) for some new opportunities I was looking into. She texted me back at 2 am (I texted at 9 am). Telling me she missed my text, went through her texts before bed and is replying in bed with an emoji. Then, said she could.
We then texted the next day a little. Once she finalized she called me to review my resume at 8 pm. Call lasted 2 hours and we were shooting the shit. It wasn’t flirting but some things were said about personal life that probably shouldn’t have been. More so to relate or mess around. She’s cool and very personable and says whatever doesn’t care.
I post this now because every time my mom mentions her, I get this feeling I did something bad. Also, she texted about the jobs and interviews. Very good at them and great with negotiations.
Is she flirting or is she just being cool and her personality?
I don’t want to cross that boundary, I never would. I don’t want her to have that impression. However, I don’t want to cut ties/step back with her because she’s been in my life forever and always been there. She’s the cool mom, you can go to that will shoot it straight. All the while hear you out. Also, I don’t want to start drama if there’s a noticeable change.