I know the title sounds bad but I’m having a hard time telling if I’m actually in the wrong or if I’m just being a doormat. Basically, I (F, 23) have a friend from college (M, 24) who finished his classes in the winter, but isn’t graduating until the summer. Our university kicked him out of his housing over winter break despite the fact he was technically a student.

After this he lived with mutual friends of ours for about 2 weeks before winter break ended and they could no longer house him. They told him from the beginning that they could only host him for two weeks.

Despite this, when the two weeks ran out he messaged me and asked if he could stay with me, basically only giving me a nights notice. I felt bad and agreed, because I didn’t want him to be on the street when I have an open room.

The first mistake I made was not setting a time for him to move out immediately. Because of this, he ended up being there for about a month before I sat him down and told him we need to have a plan because I cannot host him indefinitely.

I explained to him I can’t offer to rent him the room because my lease is also against subletting, and I have roommate on the lease who is not currently in the apartment, but is still paying rent per her terms. I told him that he should plan to find a new place within 2 weeks. He agrees. The time passes and by the time the two weeks are up, he has given no indication that he’s figured it out and was avoiding me by staying in his room. I waited a day to see if he would approach me about the situation, but when he didn’t I asked him his plan the next day.

He told me that his job offers didn’t pan out and he needs more time. I’m fed up at this point but just say fine and tell him to keep looking. More time passes and I sit him down and tell him that I know I was too lenient with the last deadline and we need to set up a final one. I asked him about his apartment search, and he admitted to not having looked at all. I told him that’s not acceptable, especially because I had sent him links to apartments to apply to and told him about apartments in the area I know are affordable and leasing.

He told me he thinks he needs another month to get it all figured out. I was extremely annoyed at this point and told him he has two weeks and needed to be out by Friday when the time has passed. He did not come out of his room for like a week after than and completely avoided me. The Friday came and I asked him his plan. He told me that I had given him until the weekend. I told him that I never agreed to him staying over the weekend, but said he could have until Sunday if that’s what it took for him to actually leave.

Now it’s Sunday and he’s saying he thought I meant he had through the weekend and was planning to leave on Monday. He has a place set up for Monday, but I’m annoyed he’s staying here another night in the first place when I set clear expectations and already gave him an extension. I know I’ve been a doormat throughout this whole ordeal, but it’s a tough position and I don’t have much experience with putting my foot down with people.

Would I be the asshole for making him leave tonight, even though he hasn’t figured out housing until tomorrow? It’s been almost three months of him living here rent free at this point. I’m just worried he’s giving me BS and will try to stay even longer if I don’t put my foot down. I know I was an incredible pushover throughout this process, but I have also been in situations where I’ve been homeless and had nowhere to go and have a really hard time putting someone else in the situation, even just for a night. I even told him of shelters in the area and told him to reach out and he didn’t.

I feel bad not wanting him here, but he makes me uncomfortable in my own home and I don’t want to feel like that. I can constantly feel him staring at me and have caught him multiple times. He’s also made comments that make me worried he has a crush on me, which adds another level as he’s a single man and I’m in a committed relationship. He also riles up my dog on purpose and when I tell him to stop he just says “it’s fine”. I just hate feeling uncomfortable in my own home and it’s gotten to the point where seeing him at all just makes me mad. WIBTA?