Women of Reddit, what is your worst 'Nice Guy' experience?

So this is going to be a long one. Hold onto your butts guys cause here we go. I’ve been friends with this guy (we’ll refer to him as Jay) for almost 10 years. I met him when I was 15, and he was about 18 or so. We had mutual friends, and went to mutual parties. At this point I was dating a guy (we’ll refer to him as Goob). SO FAST TRACK TO ABOUT A YEAR INTO THE FRIENDSHIP, we are drinking and he leans over and tries to kiss me. The first time I moved away and said “What. The. Fuck. Bro.” To which he responds by trying to kiss me again. Bear in mind that Goob was on his way back from picking up another friend of ours. So I got up and moved to another area. FAST FORWARD ANOTHER YEAR. Goob and I were having problems in our relationship, and we decided to take a break. So Jay decides, not even a week later, to profess his love for me. I decline. So he turns to another friend of mine (we’ll refer to her as Chay), and basically tells her that he has feelings for her and wants to date her. She declines. FAST FORWARD ANOTHER YEAR. This year there wasn’t a specific allocation of his feelings towards me, but rather to everyone in our circle of friends. Goob and I are together, and I have everyone telling me how Jay still has feelings for me, and I should watch myself around him. At this point I should say that I had never given him a gram of leeway. I never sat next to him, I never touched him (other than the Hello/goodbye hugs that we all did) and anytime he made a comment that was even remotely sexual I would verbally say “Ew.” Or “Gross.” Basically, there was no misconstruing my actions for romantics. FAST FORWARD ANOTHER YEAR. This is when he started to make comments towards me about Goob. Traditional, “He’s no good.” “He’s a bad person.” “You know I’m here for you.” “I would never do that to you.” I mistakenly took this for friendship, pushing away the reality of him being predatory. I have a lot of patience for people, and I am very forgiving. Also, around this time, he was still attempting to date Chay, having his efforts rebuffed, and then turned his sights to another one of my friends (we’ll refer to her as Mag). Mag and I had been friends longer than I had known Jay, so she tells me of the inappropriate vibes she was getting from him. All the while, she started dating someone (we’ll refer to him as Turd). FAST FORWARD ANOTHER YEAR. Goob and I had broken it off again, so naturally, this was the year where Jay told me, again, that he was in love with me. I explained to him, again, that we would not ever be together. Our friendship was important to me as we had created a good one through our interactions and our mutual friends’ interactions. So, he goes to Chay to try again. She declines him again and he tells her, “Yeah. Its cause I wanted {me} the whole time and I couldn’t get her” So here’s the part where I say that he has a disease that most people die from by the time their 40 if they don’t take care of themselves. Which he doesn’t. So he also tells Chay that he wanted to be with her cause he thought he was “going to die soon.” So then he goes down the list to Mag. He asked her out, while she was still in a relationship with Turd. FAST FORWARD ANOTHER YEAR. Jay found a girl who’ll kiss him! Rejoice people, cause it was a breath of fresh air. We’ll call her Kay. FAST FORWARD ANOTHER YEAR. Their relationship ended. Boo hiss. So in his turmoil, I helped him process the break-up, because that’s what friends do. Of course, he saw this as another invitation to fabricate feelings. At this point Goob and I we’re on and off again, and every time we had an argument, Jay would come out of the shadows to spew his rhetoric of how Goob was terrible and he would never do that to me. Thanks Jay, but no thanks. FAST FORWARD ANOTHER YEAR. At this point in our friendship, I saw him as a brother. Even through the uncomfortable moments, he was a good friend. I was on good terms with his parents, and it was like a second family. This is the time where I became a substitute teacher. I would call him and tell him of all the cute kids and daily adventures. After a couple of weeks, he goes to Mag because his burning love for me was unbearable and he needed advice. He tells Mag “I’m just so proud of her for doing what she wants to do in life. She’s so good with the kids, and she would make a great mother. I can’t wait until she has my children. (BACK THE FUCKING TRUCK UP) I’m getting older, and I just don’t want to wait anymore. I want to tell her how much I love her.” To which Mag replies, “NOOOOOOOOO.” FAST FORWARD ANOTHER YEAR. My dad got cancer. Goob decided that he was going to leave me for a 19 year old cause “She has less drama.” BYE FELECIA. Jay was there to help me take care of my dad. It was just me and my father my whole life, and we didn’t have any family here, so Jay would pitch in where he could. 5 months later, my dad passes. Lots of crap going on. FAST FORWARD A YEAR LATER. Goob finds his way back into my inbox. After a few months of communication, he found himself stuck between a rock and a hard place. I told him that he could stay with me until he got back on his feet, HOWEVER we were not going to get back together. Jay has issues with this and he is vocal about it. Especially in the instances where Goob and I would argue. But, I am an adult, and I do what I want. FAST FORWARD TO PRESENT DAY! So about four months ago I started dating a guy (we’ll call him Bob). Bob and I had a whirlwind month-ling fling before he went into the Navy. So Goob moves out cause he can’t handle it. EVEN THOUGH I reminded him A LOT that we were never getting back together. (He even said one time that he did things for me because he thought it would “soften me to the idea of us getting back together”.) I talked to Jay throughout this endeavor about how I felt betrayed and used because I entered into the roommate status with the understanding that a romantic relationship was not going to form. Goob had other plans, and with a “whore” here and a “bitch” there he was gone. TWO WEEKS after Goob leaves, Jay and a couple other friends are over. Jay calls me into the back room and says “Will you go out with me?” Before he even finished the sentence I said “No.” I tried to change the subject. The next day, he is texting me saying that he needed to explain himself. So I call him and he all but breaks down saying that he loves me. “I just love you dude. I…uhg, this is harder than I thought it would be…I don’t know. I just love you. I’ve loved you for years.” Be still my beating heart, bro. At this point I broke. I explained to him all of the reasons why it made me uncomfortable. I explained to him all of the reasons why I would never be with him. I explained to him that I was tired of hearing about this every year. I tell him to leave me alone because I am so angry that I do not want to talk to him. The next few days, he’s texting me. I explain to him again that I do not want to interact with him. He says, “I don’t understand why you’re so mad, a little freaked out maybe, but not so mad.” And “I thought our friendship was strong enough to get past this.” You can’t just take a giant shit on our friendship and then turn around and act like it doesn’t stink.

/r/AskReddit Thread