I know we've had a few of these topics but I'm going to do another one because I can't get this one situation out of my head.

On Tuesday I was in the city for a doctor's appointment and to meet a friend for dinner.  I had time to kill so I decided to check out the LGBT community center simply because I've never been there before.  Besides they have free wi-fi and I had my netbook with me.  There were a bunch of little tables with two chairs each in the main hall.  I sat down and got out my computer and then suddenly there was a guy sitting across from me.  He announced that his friend abandoned him and now he was going to talk to me. 

Immediately I could tell three things.  First for I could tell he was attracted to me and this was actually a pick-up.  Which is always flattering and naturally I don't mind.  Second there was something not quite right about him.  I mean that in the nicest way possible.  Having two boys with autism one severe was what gave me the patience to deal with him in the first place.  Lastly he smelled to high heaven.  Really bad body order as if he had not showered in a few days.  Also his clothing was not nearly warm enough for the weather.  He said he was 20 but could have been lying.

Before you think homeless he said he lived with his Mother and even called her on my mobile at one point.  Perhaps even that was an act.  He started to talk and talk and talk and he would not stop.  It wasn't long before I just wanted to be left alone.  I know he was trying to impress me.  I tried to be patient and polite with him because I could see he was lonely.  My parental side came out and I just wanted to take care of him.  I had no attraction to him at all.  To me he was a little boy because that is how he was acting. 

A few times I managed to get him to leave but he would always come back.  As he talked the conversation got more and more sexual and he was dropping anvils left and right.  Then he asked me out right if I wanted to have sex with him.  It was so awkward and I just wanted him to go away but at the same time I didn't want to hurt his feelings.  Eventually I shook him when I walked out of the community center myself.  He gave me the saddest puppy doggy look I've ever seen as I left. 

Now I can't get him or the situation actually out of my head.  I've talked to my partner and my male friends.  They all agree that I should have told him to f off immediately.  I just couldn't because I felt so bad for him.  They claim that was empathy and a female trait and I need to drop it like a bad habit.  It's kill or be killed out in this cold world and it was not my job to take care of him.  I would like to believe if it had been someone who was clearly more together I would have no trouble asserting myself.  However perhaps not and that doesn't make me feel good at all.  I just can't get over this hump of wanting to please others.

This is leading me to question my masculinity because I do have this huge caring side that was obviously taken advantage of.  How do I turn off empathy so this doesn't happen again?  What would you do if you just wanted to be left alone and this obviously troubled and lonely kid wouldn't stop hitting on you?   

Empathy is considered feminine but seriously I have met guys who had stronger emotions and more caring than I did so I don't really believe that. I think you did the right thing. I would've put up with him for a while but as soon as he brought up sex I would've said I'm not into sex with strangers and if he didn't get the hint I would've probably told him to F off because I would've be uncomfortable and I tend to do that to people that make me uncomfortable like that

Thanks Michael. 

I'm just looking at my response to the situation and seeing it as almost entirely female and that bothers me.  Without a doubt I am much more content being regarded as a male by myself and by others.  Just things like this make me wonder how good I really am at it.  Even this whining about it is female. 

Damn it 

My dad was about the manliest man I ever knew and he had an empathic streak in him a mile wide.

As to the weirdo dude. Yeah you should have told him to f off...
just sayin'

I can be quite empathetic at times but I would have told him to f off right away, or straight up left.

I'd tell him to F off, honestly. (Then again, I'm not the nicest of people.)

Also, I've known guys who are ridiculously empathetic. Don't worry so much about it.

It's ok to be empathetic. Empathy being a female trait is just another stereotype.
But to save yourself from this awkward situation but to not hurt his feelings, just politely decline, say goodbye and leave.

I think anyone who has experience with autistic young men would have responded with empathy to this guy. I don't think this is a male or female thing.

I've worked with developmentally disabled men and women, and I don't know how long I would have remained comfortable with the lack of boundaries part of it. I think I would have said something very clear earlier on that you were not able to talk, I certainly would have spoken up earlier in the sexual aspects to say, "I am not comfortable when you talk about sex. I must go now" and left.

I think the problem is that the way you tried to deal with your empathy and compassion was a feminine style of not wanting to blow him off, make him feel bad, or "be a bitch." Except as you likely know, it is pretty certain that this young mand wasn't capable of understanding subtle brush off or clues that any regular guy might. You don't do him any favors by continuing to talk to him when he is dropping his anvil comments, because he thinks he is "chatting you up" successfully. Someday, some other guy MAY tell him off, punch him or react with violence, and I think the best way to react with empathy and compassion is NOT to be that guy or to give him the brush off you'd give a normal persistent/creepy guy. It's to make it clear in no weasel terms that his behavior is not acceptable and could be dangerous to him in the future.

I probably would have responded similarly to how you did, as I'm also very empathetic. I've been in a situation like that before, and just left because the person tried to kiss me. 
As for questioning your masculinity, I've always associated empathy with neither femininity or masculinity. It's something that is just "human" to me; a genderless trait. Obviously, in society it's more ingrained/acceptable for men to repress those feelings and women to be in tune with them...so I understand why you would feel that way  .

Caring is genderless. everyone should care.

That said, yeah you should have told the stinky little goblin to f*** off. If you don't chase stinky little goblins away they'll harass you until you need to get the police involved- and sometimes they need to be rejected to learn to respect you and then you can actually become friends and convince them to shower once in a while.

There's a guy at my LGBT center who is a little like the fellow you encountered. I'll be sitting in the lobby, waiting for a meeting to start, and he'll come up and start talking to me. I will let him ramble if I haven't got any work with me. I know he's not quite "right" and probably doesn't get much positive social contact.

If I have grading obligations that I must fulfill, I'll let the guy talk for a few minutes, and then I'll tell him that I brought work with me because I really have to get something done. He accepts this. But I give him some strokes first.

The guy you were dealing with wouldn't have been so easy to shake, obviously. I would have talked to him for a few minutes; then I would likely have found a good opportunity to kindly say, "Sorry, it's been nice talking, but I really came here to get some work done." If he kept pestering me, I would be firm but patient--to a point, and then I would mention him to one of the guys at the front desk, and let them deal with him. Does your center have staff like that?

Empathy is not a female trait, but I think a lot of straight guys have drunk the Flavor Aid and don't respond empathetically very often, at least not in any obvious way. Plenty of guys in my gay group are very empathetic, possibly because they have been through the wringer and have been able to throw off some of that early "male" conditioning. Or maybe they never had it to begin with.

There is nothing wrong with your being kind, especially considering your family experiences. But you seem to want to be more assertive. If that makes you happy, work on it. If not, keep going as you are. In my opinion, the world needs more gentle men. You just don't want to let too many people walk all over you because of it.

My therapist, who is gay, is the most empathetic man I know. Yet he's usually read as straight!

Thank you for the feedback everyone.  I'm just going to have to mark this one down as a lesson learned.  I should give myself a break and realize that a transition is a period of moving forward.  I can't be expected to know how to handle everything straight out of the gate so to speak. 

A big part of me agrees with Sean in that it would have been kinder to teach him a lesson then indulge him in the long run.  I was just unprepared but I suppose it happens.  Next time I'll be much more direct before it goes to far. 

Arch regarding the staff at the center they kept an eye on us watching for a signal from me.  They were obviously uncomfortable but didn't know what I wanted.   I normally don't like to ask for help from anyone but I probably should have in that case.