Should I end the situation or stay friends with boundaries?
(37F) I’ve been “seeing” a woman (39F) here and there over the span of two years. We started dating when I was single for 4 months, then my ex came back around and I gave him another chance. I broke things off with her and was honest about my reasons beyond getting back with my ex. We decided to be friends with his blessing. Her and I hung out maybe twice as friends when I was with my ex. My relationship with my ex ended horribly and she was a distant yet consistent support to me. She is often out of town for weeks at a time, so offered her place to stay.
I ended up moving out of town to start over. I knew no one and have had no plans to date anyone since. She stayed consistent with her friendship and communication. One time she drove two hours to see me for a few nights. I wasn’t sure what the nature of it was. We slept separately the first night, then drunkenly hooked up the second. It was nice and kind of broke the awkward tension. The next time I saw her we went on a Mexico trip and then to the city where I met her close friends.
It’s been about 9 months, I got a job back near the city, so moved in with family. Right away we made plans. We hung out marathon style every weekend. She insisted on picking me 30 mins away, she brought flowers for my mom and talked with my parents while I got ready. Then we went out and she bought me some jewelry I was trying to buy for myself. She literally wrestled with me to pay the guy first and ended up throwing cash at him. On this outing, she said for the first time aloud to someone else that we are dating.
I was grateful for the rings and all she’s done for me when I was down and out. Now that I have a job, I bought us ViP tickets for a show. We went, it was fun, then we went dancing after, also fun. But I drunkenly had the courage to ask the what are we question… she said, “idk, I thought we were just having fun.” I couldn’t be mad, my ego was bruised, I never decided myself if I wanted to date her either.
What bothered me is how she insisted on sentimental extra things like meeting my parents, buying my mom flowers, and buying me rings that weren’t cheap… saying we were dating to someone else. All of it. I sometimes felt guilty taking anything from her because I was never sure what her intentions were. I brought it up to her and she basically said she’s sometimes thought maybe, but it’s never been the right time because I just got a job and I’m focused on school. She said she’s always been rooting for me as a support. She said I was right to bring up the mixed signals, but she never knew if I wanted to date-date either.
Now it just feels like she was over giving to mitigate her guilt for not wanting to date me for real. It feels like I’m a pity project, or worse, an unwitting sugar baby. Doesn’t feel good. I’m not sure if we were ever friends now.
I’m extra hurt because this has been a theme in my life. I had a bf from an affluent family who basically told me I wasn’t good enough because I didn’t have an education. What I hear is that I offer no status—I’m just a good time girl. Despite being independent for 20 years before recently when I started over and went back to school, I was never good enough for anyone who enjoyed my company and said they cared for me. That’s not good enough for me, but it still hurts.
Idk am I right to feel this way, or am I ruining a good friendship over bruised ego?
TLDR/long time situationship is confusing, and I don’t know how to pull away or if I should end it all the way. Not sure if I’m right to feel this way
Posted Sep 29, 2026, 2:30 AM UTC