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Creepy Colleague

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Bright:
I'm posting this for my sister, who wants to step into a situation to help a friend out. While this is a situation that involves two of her workmates, they're also her friends and it's happening outside of work so I think it's more suitable for this forum.

My sister works with a man named Bob, who she says is a nice guy but rather socially awkward. Bob catches the bus home right outside of work.

My sister's friend, Anna lives a 15 minute walk away from work. Bob has taken to walking Anna home. At first he asked her if he could and she said yes. Keep in mind that walking Anna home involves him walking the 15 minutes to her house and then the fifteen minutes back to work so he can catch his bus home. This has got into a pattern where he's walking her home every day, without asking her first if she wants his company. Some days he'll speak to her. Some days he'll just follow behind her the entire way home without even saying a word or trying to communicate.  Anna does not live in a dangerous part of the city where she might need an escort, and walking is a perfectly normal form of transport here especially such a short distance.
 
Anna's boyfriend is not happy with the situation and as much as he'd like to put a stop to it but thinks it's a situation Anna should be dealing with herself. Anna doesn't know how to approach Bob about it, she doesn't like confrontation and she's more likely to just continue to tolerate the situation without actually doing anything about it.

My sister's offered to help out. She thinks Bob's a bit starved for friends and that he's latched on to Anna for the social contact (he's aware Anna has a boyfriend and my sister doesn't think he's interested in Anna in that way) and he's unaware of how weird and creepy it's coming across. (He's done some other things which are also rather weird/socially awkward but they're not relevant here.)

My sister is on friendly terms with Bob. She doesn't want the situation to escalate to having to speak to management about it. (Her work doesn't have a human resources department). She'd like to speak to him as gently as possible, as a friend, so he doesn't get offended and tell him he's being a creeper and he should stop stalking Anna home.

When she was discussing the situation with me, asking for my input I offered to post it here to ask for some other opinions.

Does anyone have any suggestions on how to handle this and what she should say? 

yokozbornak:
If Anna doesn't like Bob walking her home, she needs to put on her big girl panties and tell him so.  It sounds like he asked permission to walk her home and may be worried about her safety.  It's up to Anna to let him know that his help is not needed.  I certainly don't see a reason for anyone to go to management or to have a friend intervene.

If Anna talks to him and asks him to stop, and he continues to try to escort her home, then she has a legitimate cause to complain. 

lowspark:
Yeah, I agree. Anna just needs to say to Bob, "Please don't walk me home anymore. I'm not comfortable with that." Period. Your sister needs to stay out because really it's not her business and who knows how Bob will react or interpret her involvement.


--- Quote from: yokozbornak on July 02, 2012, 12:33:25 PM ---If Anna doesn't like Bob walking her home, she needs to put on her big girl panties and tell him so. 
--- End quote ---

This. Exactly.

Belle:

--- Quote from: yokozbornak on July 02, 2012, 12:33:25 PM ---If Anna doesn't like Bob walking her home, she needs to put on her big girl panties and tell him so.  It sounds like he asked permission to walk her home and may be worried about her safety.  It's up to Anna to let him know that his help is not needed.  I certainly don't see a reason for anyone to go to management or to have a friend intervene.

If Anna talks to him and asks him to stop, and he continues to try to escort her home, then she has a legitimate cause to complain.

--- End quote ---

This. It sounds like Anna hasn't actually asked Bob to stop walking her home. She needs to do that. "Bob, it's kind of you to make sure that I get home safely, but I'm really fine walking home by myself. From now on, I can walk home alone."

Teenyweeny:
Anna needs to approach Bob about this. Yesterday, because there is something wrong here.

I'm a socially clueless person. I can see walking with someone, thinking that they enjoy my company, or that they feel safer, and not getting their cues. But following them? That's plain creepy.

"Bob, I have to ask you something. Please, don't walk me home any more. I prefer to walk home alone."

If she notices him following her, then she needs to turn around and say,

"Bob, are you following me? Dude, you know that's creepy, right? Go away!"

If she doesn't feel it's safe to take that approach, then that's a sign that she needs to involve management, pronto. Personally, I'd involve management right now. Normal people don't follow their colleagues home. No matter how 'clueless' they are.

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