There is a younger man I know who I’ve casually befriended at work. We began working at the same company at the same time and have the same ethnic background. I’m 43 and he’s 27. We don’t chat daily or exchange lots of intimacies. Every 3-4 weeks, we would go out for lunch when we were still working from the office, and maybe once a month, we’d do happy hour. I think he has romantic feelings for me, and I’ve told him that nothing was going to happen between us since I have a policy that I don’t date people I work with. Plus his age makes me wary to get more involved with him even though he’s physically attractive. This guy is extremely socially awkward and doesn’t pick up on cues or lack of reciprocal investment from others that well, so even when I never initiate anything with him, he’s always trying to get together with me and I keep rebuffing him. He moved into my apartment complex about a year ago, so he can see my comings and goings. For whatever reason, his thoughts have led him to want more close relationship to me than I want. When he thinks I’ve been rude or not responsive enough to him, or if I tell him how he’s annoying me by continuing to ask me to do things when I don’t want to, he tells me what I did wrong, makes a big show of telling me he’s going to block me from contacting me (I never contact him) and then he comes back later with an apology. He has a completely different take on the relationship than I do. I took pity on him when I first met him because I can see he struggles socially and cannot be friends with girls before quickly developing feelings, and didn’t really think he’d develop feelings for a woman 16 years his senior – he has no life and no passions and no real interests. When we do spend time together, I don’t want to spend loads of time with him because I don’t feel like he’s adding much to my life and I’ve privately made the decision that socializing with him is mostly time wasted that I’d rather spend on Thought Work, cooking, reading, exercising, developing other friendships, taking online classes, etc. Even though I’ve told him to stop asking me to do things with him and have stopped responding to text messages, he continues to try to reach out to me via work instant messenger. I ignore those messages because I think I’ve been clear in telling him where I stand with this friendship. The conversations we have are the kinds of things you’d talk about with a little brother. I don’t know how to get rid of him. Part of me judges him. I know he’s having a hard time, but him doing dramatic lashing out at me and then coming back looks crazy to me even though he likely believes that I’m hurting over his behavior. I just don’t respect him and think he’s young and kind of clueless and doesn’t bring much to the table that I’m looking for. I have been considering moving away from this apartment complex. He finds a way to contact me every three weeks. I’m very close to responding to him in an incredibly insulting way because he just doesn’t want to get the message and doesn’t realize how crazy he’s coming off. At heart, he’s a good guy, but his behavior is annoying and I’m not interested in dealing with him. I want to feel like I can send a message to him and get him to stop contacting me, but he’s not complying with my manual. Because I can’t block him on work IM, I can’t really just take care of not wanting to hear from him by blocking him. I’m not responding to him through any means of communication. I know that he’s not respecting my boundaries, but I can’t help but feel enraged when he continues to try to get my attention even though I know he’s just a clueless kid with good intentions. He’s not learning how to handle his emotions. I’m not sure if I should reiterate my boundaries. I feel like he moved into my apartment building and keeps trying to make contact even though I have not invited any of this and don’t think he will respect my boundaries.