How do I (23F) help my friend (26F) who is stuck in a situationship cycle?
For context, my friend broke up with her ex in July 2025. He wasn't a terrible person but he refused to take care of his mental health and borderline neglected her. She stayed with him for almost 3 years out of hope he would get better, despite the fact most girls would have left him after 5 months max. This is only to show that my friend is the type who hates being lonely (she has admitted this) and will stay for longer than she should.
Fast forward three months and she was messaging somebody (36M, so 10 years older) who she occasionally worked with. He initiated first and straight out of the gate was sending her flirty messages, mostly sexual. I told her that this probably indicated he just wanted to hook-up or be casual as opposed to a relationship, but she wanted to try anyway which I don't blame her for. They hung out for the first time and had made out. Then she spent a weekend at his place when he revealed that he had got out of a 10 year relationship 9 months ago, and wasn't mentally ready for another one just yet. She assumed this was the end and she was DEVASTATED.
The next time she saw him, he clarified that he still wanted to see her, but going "slowly" and "no-label". She was more than happy for this as it meant she got to see him more, and thought eventually it would become a relationship.
I'll try to keep the rest brief, but they had a pretty intense situationship over the next few months. At one point he experienced multiple bad events affecting his mental health, and cut things off with her (he said he "wasn't the right guy for her" probably realizing how much she wanted a relationship). They started back up again a month later LOL. After things eventually got intimate, she brought up a relationship and AGAIN he said he wasn't ready, so she decided she needed space since it was hurting her to be with him. However, he told her that he still "found her attractive" and "liked her in that way" so she STILL had hope (she had already wasted 4 months with this) so it was hard for me to see. This was the end of February.
Even with the "space" she was still texting with him almost every day. Her plan was to keep things chill, then ask him again in June before "FINALLY" moving on. But last night they hung out again because they have been flirting lately over text messages and got slightly intimate. Even though I told her beforehand she is basically giving him everything he wants, which is not going to give him a reason to want a relationship. Now she is even questioning the "June plan" due to this and is debating to just see where things go.
I've already told her that it's a low chance they ever get into a relationship, and that he's 36 and knows what he wants. If it was a relationship then he would have made it happen already. She takes pretty much everything he says at face value, and frames him as this highly sympathetic person (he is not that). Admittedly though, he treats her well when they see each other (which she’s not used to from partners) but it’s not anything most other guys also wouldn’t do. I just don't know what to do anymore, as it’s taking a lot of energy from me, but at the same time I don't want to lose our friendship over this. She's a great person but I feel like I'm watching her bang her head against a wall over and over.
TLDR: My friend is enamored with her situationship and refuses to see the possibility that they will never actually date. I'm not sure how I can help her anymore.