Sister strange situation

Location: Cook county Illinois

So my sister been dealing with a guy for 6 years and they broke it off. After the break up he’s made attempts to reach out to her via calls,text and email to persuade her to have a talk with her. She would respond sometimes. She claimed he was cyberstalking her. Claimed he put cameras up at her property. She she feared for her life if she see him in person. So I thought the guy was on some Stalking stuff. She had thoughts of a restraining order.

2 days ago I ran in the guy at the car wash he spoke to me and was friendly. He didn’t speak on what happened with my sister but I had to ask to hear his said. Come to find out he told me and showed me texts when he asked what could he do to get back together. My sister wanted $8000 from him to get back together. I seen the cash app and zelle request and everything from her and installment plan. And he show me the text from her saying don’t talk to me till you have the money. My sister claimed he was spoofing numbers and left voicemails when she didn’t wanna talk to him. But he told me it was only to give her back our house keys,her extra car keys and her personal items to avoid future troubles . Hit me with that old saying it’s 2 side of the story.🤦🏻‍♀️

After speaking with him he claimed he already gave her everything back and don’t wanna communicate with her anymore.

Would my sister still be able to get a restraining order? I really think she wanna do this because he didn’t give her the money. And I highly think my sister was gonna take his money and run.