Shy, insecure, borderline depressed girl

[ChandlerSanzone]

This girl I'm living with has a boyfriend who lives 3 hours away so the odds of us becoming anything is quite slim; however, I want to use this opportunity to become less of the stereotypical "nice" guy. The girl I'm living with has social anxiety so she is terrified of social interactions so she has no friends within a 200 mile radius besides me. She is also super insecure and (I think) depressed - she thinks that she is ugly and worthless and she constantly complains about how lame she is and how terrible her life is.

My questions to you:
How should I respond when she comes to me complaining about things?
How should I respond when she comes to me talking about her boyfriend (should my responses be different depending on if she is talking about her boyfriend in a good/bad way?)?
How should I respond when she asks me for my opinion about things that I don't care about/portray me as the "gay best friend" (what should I wear? is this shirt cute? etc)?
She wanders into my room a lot and clearly wants me to hang out with her (since she has nobody to hang out with), but I don't want to hang out with her like a gay best friend would...what should I do?
How much should I do for her? She is my roommate but I don't want her to think I can just be walked over...

I hate listening to her wallow in her own self-pity but I do feel bad for her at times. She talks to me about everything and I DO NOT want to be just a shoulder to cry on for her. She tells me that she's surprised I'm single because of how "nice" I am (trust me, I know this is BAD). I want her to stop thinking I'm "nice" and I want to have her respect me as a man.

ANY advice/tips helps, thanks in advance everyone!

 

[razir110]

Convert her into your wing-girl! This way there will be less boring hangouts and less whining about her Bf.

Would be a sweet one to pull off!

 

[SexAlchemist]

My experience with girls like this is that they will keep harping in their depression and things that suck in their life quite often when you two speak with each other. It's very difficult to not empathize and fall into the trap of being the nice guy with her when this happens. And if you try to just be neutral about it, she'll still keep bringing up how depressed she is, and it's almost impossible to not talk about her issues again.

There's a girl I recently went out on a couple of dates with that was like this and I tried to "save her" by recommending therapy and various other things she could do to help herself or something I could help her with because I genuinely wanted to help her, but I realized that I was going to end up bringing her attraction for me down by doing so, but she was suicidal so I cared more about helping her than getting with her and did everything I could think of to help her.

In the end, she ended up pushing me away and I ended up chasing hard, but we're on good terms now and I'm not going out of my way to help her. She seems to be doing better than before because she doesn't bring up being depressed although she has mentioned that she did some drugs like ecstasy which is obviously not good and a sign of depression or her feeling out of control in her life. Despite her depression, I like a lot about this girl and would like to get with her but I know I can't try helping her like I did before, and the only way I'll really only be able to help her is if we are together.

It takes a lot of energy, time and patience to get with a girl that is in a depressed state and not in a good place in her life, and you may want to reconsider if you want to use your time and energy to do so.

 

[ChandlerSanzone]

Bump: anyone have any thoughts?