Starting to see red flags???

Hello! I am thinking I am pretty right about this guy being one of these personality disorders, but wanted to share my experience!!

Our first date he basically told me about his life in the past couple years and how crazy it had been. His mom passed away not a year ago, dad a few years ago. He had been living off and on with friends for a few years, and when we met had been staying with people who had free rooms at a casino. Also, he didnt have a car on the road because of a dwi, but did get it back on the road within a few weeks with my help driving him to the DWI. Now I was willing to give him a chance and hope he had a rough patch and would get going but I started noticing other red flags too. He was also going to school to be a dealer and wasn’t currently working at a job.

I had been single for awhile,(I am 36, he was 30, lived on my own for years, good job, and able to take care of myself) and he was the first guy I actually liked in awhile. We had great sexual chemistry and he was so much fun to hang out with. We talked/texted all the time. We ended up sleeping together within a few weeks, and he stayed over that night. Around this time I just felt something was off, and it was like he felt entitled. I also was wondering if he was a moocher. I remember going to use the bathroom in my apt. and came back to the kitchen and he was eating food out of my fridge!!! Without asking. He just seemed like entitled, like what is mine is mine, and what is yours is mine. That day he also asked if I had a shirt he could wear to the gym, and if I had a charger cord for his phone. I had a very unsettling feeling about this and just felt like he was using me. When called out on it and how i felt a few days later, he just said he wasn’t trying to take advantage of me and would never do that.

Over the next few weeks just weird comments/things happened. He was very friendly to waitresses, etc. Always calling them honey and being very outgoing. One time he even said on the way out of a resturant she had a nice butt!

Always some kind of family drama or just drama in general. Most conversations revolved around him and what he was doing that day, where he was going, need to get a job, sister was basically going to be homeless, just always something. But he claimed he hated drama.

He did admit to having a lot of anxiety and being depressed etc in the past.

He was gambler, and played a lot of poker. He claimed to win most of the time, but sometimes he said he lost. He said that by becoming a dealer that would get him to stop gambling. I feel he had a very addictive personality, before I met him he was doing pot, and drinking quite a bit.

About a month in, his birthday was coming up. He was also taking his test to become a poker dealer. We had decided to hang out after his test, we were going to pick up something, cook some food at my place and hang out for the night. He ended up getting out very late so we just wound up going through a drive through. So after we ordered, I was going to offer to pay half, and I made a comment oh how are we doing this. And he actually said in front of the girl oh your getting it!!! I was like shocked but didnt want to make a scene so I just paid. I had a very bad feeling about this, because once again he just made me feel like he was entitled and I should just do it. It made me very angry and he didnt even thank me for it! I also had made him a giant cookie for his belated birthday which he did seem appreciative and thanked me. Huge warning sign was the next morning. He stayed over that night, and I had an appt. in the morning so I went to the appt. and he stayed at my place. When I got back home, I was hungry and made myself a sandwich. I went to wake him up, and he seemed very moody. He made a comment about oh I see you didnt make me a sandwich, your just so used to being alone, and you didnt even want to pick up my birthday dinner last night! It was very hurtful, and I just shut down. I was already upset over the last night, and he seemed to just rub it in my face.

He totally knew what he was doing but because I am a nice person and don’t want to argue I didnt say anything. He knew I was upset as I said barely two words to him and he ended up leaving my apt. Later on I received several text messages from him basically saying that listen, he gets it. He wasn’t trying to mooch off me, he respects me and would never do that. He also thought making the comment about the turkey sandwich and picking up his “cheap birthday dinner” was funny but it obviously wasn’t.

Everything I had been thinking about him he texted back to me (almost like mirroring me) I just feel he knows he is manipulating me. It was just so weird that everything I had been thinking/feeling about him he said he wasn’t doing.

He also was very happy most of the time, but I noticed a few weeks in that he would appear to get moody/grumpy out of nowhere but then it would be gone again.

He was just all over the place. Every day was like an adventure for him in what he could do or get from people. In the beginning he would make a random comment about oh this person gave me this, this person gave me that. When we met he had a flip phone. A few weeks in he mentioned that a buddy in class was going to give him a smartphone he could activate. When I asked him oh what do you have to do to get that, he just smiled and was like nothing, he just is going to give it to me! It seemed to give him a lot of satisfaction getting things from people or having people do everything for him.

Honestly writing all this down has helped me to realize how awful he is as a person and I don’t need someone like this in my life. I was contemplating going back and forth because I haven’t dated anyone in awhile, and maybe I just need to be more open and understanding and give him a chance to get his life together. We all have our own issues and sometimes need time to work things through but my gut feeling is just not good about him. I don’t think he will change, I also don’t think he will follow through and get his own place to live. He probably won’t even stay at this job long if he does get it!