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Perspective: Creepy or not ? (Family friend)

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I bring this to you, DWIL ladies, because I know you all are practiced at recognizing where on the   spectrum things fall, between normal---kinda weird---crazy--or legitimately dangerous. Also if this is an issue, I'll need help deciding how to approach it with my parents.


Ok so here's the deal. Sometime when I was a teenager, my father met "Bob." Bob has always given me a creepy vibe, but for some reason, my dad seems to like him. Bob did confidential (unethical) things for the military, has been in prison a few times (but always ended up overturning the charges), and is good at *insert martial art here.* That is how he knows my dad (or because of the legal issues? One or the other). My dad and Bob do martial arts together.


Bob doesn't seem to have normal boundries. He invites himself over for the major holidays at my parent's house. He will show up early in the morning or late at night without being invited, or say he's coming over and then not come. He will make himself helpful to my family with moving, construction projects on the house, etc. He has declaired himself a part of my FOO. He leaves things at my parents house for months, even after my mother repetedly reminds him to take his stuff. My father alows this, talks about it like it's funny that he doesn't act appropriately, it doesn't bother him. It bothers my mother, but with my dad not minding, it's hard for her to do anyting about it.


Unlike my dad, my mother and I set up normal boundries and enforce them, so he acts as if he is so intimidated, like we're so tough because we don't seem intimidated by him.  I suspect that it's a flattery tecnique. 


Bob seems to be really good with little kids. He teaches martial arts so he's around them that way. I'm kind of surprised, but kids aren't weirded out by him. The only people I know who are, are adult women. That said, I'd never leave him alone in a room with my kids, and neither would my DH.


The crux of the problem:


Bob spends a lot of time with my younger brother. Bob is single and middle-aged. My brother is 16. This started when he was a pre-teen. My brother suffered a physical injury that had him in a wheelchair for a while, and he was really feeling blue (I don't like to overuse the word "depressed"). Bob started taking him to the movies a lot, etc. Bob is about the mental maturity of a 16-year-old in my opinion, in some ways, so it partially makes sense...and it's partially kind of weird. I always thought it was strange, but he also likes to hang out with my 85-year-old grandpa who lives with us, and liked to hang out with my older younger brother, who is now studying abroad.


I started to get worried when I was reading a post on this board and saw a link to a Child Safety website and read the "Red Flags."  


"Too good to be true," "Free childcare," "Takes your child places," all started to remind me of him. Especially since he's offering to take my brother to an Asian Country for summer this year. I'm honestly not sure who's paying the ticket, him or my parents.


Now that I read that, I can't unread it. I already linked my Mom the site and told her a couple of the flags reminded me of him, and asked what she thought. Do I think he's molesting my brother? No. But I think SOMETHING isn't right. This is my plan of action:


1) Decide whether I think "Bob" is a danger to my brother. (I had long ago decided that there is no reason for him to ever be alone with me, my kids, or even know my address).


2) If I decide that these are legitimate RED FLAGS I will lay it out for my father (since he's the one who lets Bob into my FOO's lives). He's let this guy have access to all three of his kids, come to Christmases, etc, so I have a feeling it will hurt him if I accuse Bob of being someone BAD. They also have business toghether. This is why I want to be sure about my level of concern before going to him. It would be implying that he hasn't protected his family. My dad wants to see the best in people. 


OR: If it's not enough of a concern for that, then I will just keep my guard up, and him out of my own family's life.


I can't imagine a good outcome from talking to my brother directly about this. 


So...is this worth raising a stink about? What would you do? Should I talk to my dad about it, even if I decide that I don't think he's EVIL but is a bad influence? That's what my friend, who also knows Bob, thinks. 


Also, I think that he is the kind of person who needs to be eased out the door slowly...he seems to be very loyal, but I would NEVER want to be on this guy's bad side. I am certain that he has taken lives before. I just don't know if he has out of the service. Yes, this is part of what raises flags for me. Sorry about all the extranious background.


I'm going to step away from the computer and let my subconscious work on this a while. I'll be back later today. Thanks for the outside perspectives. Also, I apologize, but I have a problem being able to spell. I hope my mostly good grammar makes up for it.


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