Okay so I'm a virgin and this girl knows this. She also knows I'm working on a fear of girls. Anyways despite her knowing this information I figured I'd ask her out to coffee just to hang out. My friend says I'm a pussy and I should try for more at night time. I believe I read somewhere that if you ask a girl to hang out she immediately thinks "This guy wants to have sex with me."... anyways I just wanted to get someone's opinion. Should I just ask her to hangout at lunch or should I take my friend's advice? Any input would be greatly appreciated.

You want to have a friend or a girlfriend? If you just want to hang out, you will just hang out.

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You can't buy sophistication.

She seems like a nice girl and I'd settle for friends, but I'd certainly prefer a girlfriend.

Also to be perfectly honest I feel that she has only spoke to me out of pity. Even if she agreed to meet me I think it would still be out of pity. She knows a friend of mine and he told her a little bit about me before I contacted her. I didn't know that at the time though.

If you just want to hang out, you will end up having a friend. It's simple as that. If you want to have a girlfriend, well, show her that. Being a virgin has nothing to do with it. Sex just happens after you made the right actions to have her as a girlfriend.

And most of the time girls will think that you are asking her out as part of a potential romance situation. Your brother is right.

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You can't buy sophistication.

Can I be honest? Why do you think she would not be interested? The only thing that I'm reading is negative things about yourself. It's completely self-defeating. And again, your sexual inexperience has 0 to do about communicating with girls. It has no relevance, it's only an issue in your own head.

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You can't buy sophistication.

Thanks for replying. So basically my choice is risk scaring her away because she isn't interested or play it safe and try to make a new friend? I mean if I did ask her to hang out at 1am she pretty much knows the deal, right? Even if she does pity me like I think she does she's gonna think I'm looking to get laid, right?

Well, I think she is into my friend (but he has a girlfriend) and she just spoke with me to be polite. She says I'm too negative, but I can't help it. Do I think I could make her interested? Yes, but if she's not interested and she's just being polite because she knows my friend then I'm dead in the water.

1. Again wrong thinking. A girl will not hang out with you at 1 am if you are a pity person. Girls say yes because they are curious and excited.
2. You will not scar her. Girls have the same needs as you. Just relax, be playful and try to get closer without jumping the gun. That's all. It is that simple! Girls are not made of glass, they have desires. You just have to discover these and act upon them. If you have the urge to kiss her and everything is ok, well, just do it. You are not committing a crime, you are creating something wonderful.
3. Do not engage with her like she's an old friend. Because you want to have a girlfriend. If it still does not work out, just say you are cool about it. Just show you can handle the situation in an adult way.
4. There is a difference between "Yo whore, I want to bang you all night" and just giving some signals of sexual interest. And for god sake, mix some humor with those signals.

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You can't buy sophistication.

Again, self-defeating thoughts. These thoughts will determine your actions, and your actions lead to having a friend.
You do know why you are a virgin? Because you make a big deal about it. Being a virgin does not equal having a sticker on your head saying "loser". Get rid of those thoughts, and quick.

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You can't buy sophistication.

Alright, I'll try to stop thinking at everything so negatively. Thank you for the advice.

Ok, so I asked her to hang out and she said yes. However she clearly started she just wants to be friends with me. So I have a few questions now...

1) Should I accept this? I know girls don't always say what they mean...
2) When should I ask her to hang out?
3) Is there any safe way to know if I'm dead in the water without losing the possibility of her friendship?

My first question is: how the hell did you manage letting her say that ... Because I think you did something wrong before you asked her to go out.

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You can't buy sophistication.

Well I spent the first two days talking about how I was a virgin scared of girls before asking her out a few days later... I certainly dug myself a hole and I know this, but I can't really take it back now. When I first started talking to her I wasn't interested in her sexually at all. *shrug*

As a start to discover the world of dating, you managed to pick the toughest situation. In all my years, I never encountered this. So do please ask a second opinion on this forum after reading my answer.

The easiest question: yes, you should hang out. When do you ask? In two days. When do you go out? In a week.

Losing her friendship: she's not your friend, you just don't want to be embarrassed. Lose the idea. Really. Or you will fail. You don't have anything to lose, just her to win.

Toughest question: 1. Mindset: do not think about the actual purpose. Just go out with her without hesitation. Do not think one moment about possible outcomes. It does not matter. 2. Actions: don't be eager to be the funniest guy/nicest guy in the world. As I read your stuff, trying to be the natural entertainer of women will not be a success. That act will end very soon if you spend a whole evening with her. It needs to grow. Just take it slow, be casual, formal but relaxed. After a while, just say one or two things that show your sexual interest. Read her reaction, just say it like you would comment her shoes. It has to blend in your topic. Even if you don't have the most positive reactions, things have changed. And just continue the conversation. After your "date", wait a while. Do not text her. Just disappear for a week. After that week, text her something entertaining. Have a little conversation. Wait another couple of days, ask her out again. With the little conversation you will know if she had a great time. If she had a great time, proceed with a real date.

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You can't buy sophistication.