Guys, I am new to all this and trying to figure out a balance for cocky and funny. I think i messed up big.

Please analyze.

The MSN chat is posted below. I put in brackets my thought process:

The chat:

Her: You were suppose to come online last night you. You dont have time for me..lol
Me: I am sex symbol at night. Do you know I have night job at a strip club. sshh dont tell anyone. Its the reason why I am on so late.
Me: ya ok! lol
Me: Serious. How do you think I have paying for school?The reason why I can't remeber things sometimes including what I was going to ask you is becuase the women in the club give me a hard time if you know what I mean. It takes me awhile to recouperate..lol
Me: Hopefully I can remember the next time we speak
Her: wow! lol i don't believe you for a second! lol
Me: would you have a problem if I was? Lets say if we were dating and you found out I was doing that..lol. What would you do?
Her: i don't think i would be cool with it
Me: lol
Her: i want my man to dance for me and no one else lol
Me: lol that can be arranged. Only for a small fee of $100/hour and you got me. Agreed? (Compliance, DHV)
Me: I wont take anything less (DHV)
Her: um no! i'll just get someone else who will give to me for free
Her: lol
Me: Please dont bring Jesse into this. Like he is a nice kid and handsome looking boy but it just aint right...lol (Cocky and funny comeback, btw Jesse is her brother)
Me: I think Jesse would rather get paid..lol
Her: that's not cool
Me: lol Jesse can come work with me. (Did not want to back down and seem like a wuss when she said "thats not cool". D' angleo says never to back down)
Me:Speaking of work whats new for you? (I tried to change the topic)
Her: work is good (i realize here she is upset with that short reply)
Her: anyways..i'm out (clearly she is mad here as she has never done this)
Her:have a good night
Me: ttyl


What should I do now? Did I go to far by bringing in her brother? I know she probably does not want to speak with me. Should I just wait or should try to initiate contact with her in a few days with something funny OR should I apologize?

Note: Based on our prior conversations I can tell she is into me.

its alright to be funny but have respect for the girl and her family.

If she told you she was going to make ur sister into a stripper you probably wouldnt be laughing

Thanks, but it obviously was not meant to hurt her. It was just playful. Look, who gets offended with "Yo mama jokes"? Okay maybe some people do but I wouldn't expect it for a sibling. Maybe she did not have a better comeback?

i mean u started off strong and its good u didnt back down but u probly shouoldnt have brought her family into it lol.

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~remember were not just picking up girls.were building a better life.~mystery.

Thanks guys! I realize now how stupid I was. As an update, I am back in the clear.

It was just cocky funny, but remember to mix it up with bits of genuine conversation, otherwise she'll just think of you as a joker and won't make an actual connection with you. I think you left it a bit long 'til you switched to a proper conversation.

~Deebo

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You miss 100% of the shots you don't take.

You basically suggested she would get a lapdance from her own brother... and your surprised she got upset?

Probably would have worked well if you'd said some guy you know she thinks is below her though!

ahaah yes but it was really funny at the time and it still is. I now know for next time to use someone else. thanks!

Deebo man, thats exactly what I was saying to myself after I finished off the convo. It was too long. I was doing well and then shot myself in the foot. Like you said I should have mixed up with some more genuine talk. thanks!