Ah, MrRight, the fine art of conversation and flirting. It's something I am grappling with as well, the only difference is the attitude.
You need to be aware that you will have many opportunities to improve on your conversations skills. You just need to find out what works and what doesn't by practice. Just as you did by talking to this girl.
It was hard to do it, and you felt embarrased, but you did it, which means you can do it again. In fact make it a point to do it more. Become comfortable in just having a conversation, but do not attach yourself to the result of it. Treat each conversation as a learning exercise.
What can you learn from this conversation I think you've already identified a few problem areas:
> (Girl keeps looking at me, nothing new)
Which shows she was attracted to you initially. So somewhere along the way you had a failiure in communcation.
> Me: "I I I I gonna sit with you."
NothinSpecial: "Sure."
Me: "Sweet."
NothinSpecial: "haha."
You made the effort to sit with her, but you could have done it with a bit more confidence i.e., not stuttering. Try practicing in front of a mirror how can you say "I am going to sit with you" with more confidence and wit. You need the confidence or wit, otherwise it sounds arrogant. In that case frame it as a question "May I sit with?"
> (Awkward/Formal Handshake)
If you are not comfortable with handshakes, then don't do them. Besides you are not making a business deal here. Just flash her a smile as you sit down and make eye contact. This shows her you're interested in her and appreciate it that she has given you the opportunity and time to talk with her.
> Me: "I'm MrRightNow, and you are?"
NothinSpecial: "Hi, I'm average-at-best, how are you?"
Me: "Decent."
There is a mental attitude problem here, that reoccurs throughout your post. You are making all kinds of judgements about this girl from this very brief and neutral encounter and nor does it help putting labels on her. You do not like it when the same is done to you, do you? Then don't do it yourself.
Everytime you approach somebody for conversation, look at them as a person and concentrate on what is being said.
>Me:"So where you from?"
NothinSpecial: "Ann Arbor, you?"
Me: "holy shit."(this is detroit)
Me: "Live on your own?"
NothinSpecial:"Yea, since I was 20."
Me:" What was the hurry to move out so quickly?"
(this is probably were she got turned off)
NothinSpecial: "I'm independent."
Me:"So you live in an apartment?"
NothinSpecial:"Yea."
Me:"Jeez, I'd rather just save up till I can afford a nice place myself."
You've identified this problem area. You asked her where she is from, she replied, and you respond with "Holy shit!" What are you so surprised about? That she lives somewhere on this planet? You immediately follow that up by criticising her "What was the hurry to move out so quickly"
You have just met her within seconds ago, and you are already asking her very personal questions.
You do not seem to be listening at all or showing any genuine interest in her. The moment she says something, you try and say something witty, instead of asking her more open-ended questions and letting her talk about herselves.
This is another attitude you need to adopt in conversation. Show genuine and sincere interest in them.
> *A joke about apartments goes way over her head*
NothinSpecial:"....."
Me: "Yea I just came from so-and-so's class."
(joke about so-and-so's mustache gets no laughs)
NothinSpecial:"....."
You've just started to lose her. She's not receptive to you anymore and is probably looking elsewhere. So you try and salvage the situation by joking about your teacher. Because she was not receptive to you, she was not going to be receptive to your jokes, especially one that is about somebody she doesn't know or care about.
There is no flow to this conversation. You start out by asking about her and she responds, and instead of taking it from there, you jump into telling bad jokes about people she doesn't know. The focus is clearly not on her. So why should she continue this conversation with you?
>Me:"What did you do before you went to school?"
NothinSpecial: "Worked."
Me:"What do you do?"
NothingSpecial:"Clean houses". (how about a job title you stupid skank)
Me:"ah, ok. How many hours?"
NothinSpecial:"25."(I work 30, but just started)
Me:"What are you studying."
NothinSpecial: something I dont know.
Me: "Whats that?"
NothingSpecial: "nutrition. What about you?"
Me:"Computer Science."
Yup, the conversation has begun to slacken. But, at least now you are asking about her, except your insincerity is probably very obvious. The subtext reads: "I have run out of interesting things to ask or say, and now I am just prolonging it"
> NothinSpecial:"Help me with my schedule."
Me:"ok."
*Now helping her*
Me:"...First tell me who teaches that class."
NothinSpecial:"Mr. teacherson."
Me:"Yea he's actually related to Monk."
NothinSpecial:"What?"
Me:"ah Tony Shaloub."
NothinSpecial:"umm yea."(has no idea who that is)
For the first time she has made an effort and asked you something - she's giving you a chance and you begin to question her about her teacher and again divert the flow of the conversation. Again, you're not listening to her. You're entire focus is on yourself.
*I start to eat and I can't split the damn tomato with my weak ass teeth and look like I'm retarded.*
If it looks as bad you say it does, then don't eat hard things in front of others, or just make a joke about it to soften the situation.
> I make a joke about the people at the school)
NothinSpecial:"...."
You could have made a joke about the situation you were in. But, you make a joke about something completey unrelated, almost out of the blue and again at the expense of others.
At this point this girl has gathered enough information to know she does not want to pursue this conversation further with you.
Here are your main problem areas, that you can work on and improve in your future conversations:
1. Listening. You will get plenty of time to talk later, but initially, let the other person talk. Show them interest, ask them open ended questions and work from the information they give you. Then ask more open ended questions.
E.g,
You: Where you are from?
Her: I am from Italy
You: Italy, that's nice. I always wanted to go there myself.
Her: Yes it is nice, I am missing my family and friends
- She's just given you another topic to discuss. If you didn't pick up on it, you could go onto start discussing Itay and the Leaning Tower of Pisa for petes sake. But she is helping you along:
You: Aww, how long have you been away from them?
Her: I've been here for 5 years now. I am studying physics at uni.
- Again, she's given you another topic.
You: Woah, physics? I thought you looked quite smart(smile and lean in)
- You've paid her a compliment, about something that is relevant and she is going to like that. However, if she didn't look smart, then don't say it, because the insincerity will come through.
Her(laughs) Oh really, what makes you think that?
- She's asking you for more compliments. You can become more flirty with her at this point:
You: You look like the intellectual type; sophisticated, smart, intelligent.
- At this point, depending on the woman you're taking to, you may have already taken the first step in the door. She could say many things to this, like:
Her: You know I was thinking the same about you(the moment she pays you a compliment, you know you've made contact)
Her: (Smiles and blushes) Thanks
Her: Thanks.
If it is the last one, then either she's shy or playing hard to get. You need to work more on your conversation. If she does not say anything, you need to make the effort. After a pause:
You: So what do you like about physics? (You conversation does not end with a compliment, the compliment was just a bonus)
Her: Well, I like physics, because I am fascinated by nature and want to study it in more depth. I've always been into that.
You: I agree with you, I find nature very fascinating myself
- This is the first time, you've actually disclosed one of your opinions. It doesn't have to be completely about the other person. A conversation is a collaborative effort, but do more listening than talking.
I could go on forever with this fictional conversation, so I'll conclude it here. Note, except for the last line, never did you divulge information about yourself or you opinions. It was always about her, and all you did was help her talk about herself and feel good about herself. She is going to remember you for that.
You've made no attempts to impress her, say witty things. You've shown genuine and sincere interest in her and maintained a natural flow of the conversation. At some point she is going to start asking you questions, just respond with the same sincerity and enthusiasm as you did with her.
2. Telling Jokes
Any joke that does not make the other person smile or laugh, is a bad joke. You're telling a lot of bad jokes by that definition. In order to tell a joke, you need your audience to be receptive to it. Have you noticed how those people who go to stand-up comedians, laugh at almost everything they say, even when it's not really all that funny. That is because they are receptive to it.
No matter how good your joke, if you tell it to somebody who is not receptive, it is going to flop. If you can't tell jokes, then don't bother. In fact you will find in good conversations, humour arises naturally, without anybody telling jokes.
All you're jokes are at the expense of others. That is not nice. I wouldn't like it, if you sat down to talk to me and started making jokes about your teachers moustache or the people at your school. You need to start making situational jokes:
You had a good opportunity with the tomato eating. It would have softened the situation. Can you joke about yourself? You could have said something like "This tomato is hard" the irony might have made her laugh.
3. Attitude
You honestly need to change your attitude. I was quite put off at the comments you made about this girl(skank, muthafuker, nothingspecial, just average) What did she do wrong? She rejected you. That her's perogative. She is not obliged to talk to you. But she did talk to you, she allowed you to criticise her, and still gave you another chance by asking you to help her.
At this moment in time, you lacked the skills to keep her as a possible friend or more, but she has helped you learn something about yourself.
The attitude you need, according to my advice, is this:
1. She is a person - keep the labels off
2. She has a right to talk or not to talk to you
3. This is just one conversation of countless conversations you are going to have in life; you will get countless opportunities. You will strive to learn from every conversation and improve and believe that you can improve. Holding a conversation is a skill, like many other skills and it requires practice. You've got your entire life to practice.
Way to see potential though. I'm done with girls, they're not worth it.
But is it just girls you are having a problem with? What you are lacking here are basic conversation and commuication skills, that will put you at odds with most people in life. So don't become resigned to the fact that you can't do it - just keep trying. Look at this, just as you would look at learning a new skill or art.
Make it a habit to talk to more girls and people in general. Every conversation for you is an opportunity to learn something about yourself.
