Facebook convo pasted here. What went wrong?

Hey, I copied and pasted this Facebook IM conversation. Sorry, it's kinda long. It started on a mutual friend's comments. She was a girl I knew from school. Always had a crush on me. She added me and this is where we picked up on IM. Thought it was going good. What went wrong?

2:18amMe

Hey, decided to move this off Jeremy's link.. ha we kinda hijacked it. I aint been out in O'Fallon for a while either (beside visiting) I'm in warrenton. Where do u live now a days?
2:22amKristina

oh im in Florissant
not too far away
Warrenton is pretty far
2:23amMe

yea, it kinda sucks but I stay outta trouble..

Wasnt your last name something else before am I trippin?

2:24amKristina

lol
yes
*%&*%#*
i always hated my last name
2:25amMe

ok, thats what i thought but thought i mighta been crazy.. lol did u get married or wut?

2:26amKristina

yes
still married just separated
I remember you from school, you were nice
2:26amMe

Yea, I dont believe in marriage.. haha idk just seems like it curses relationships..

2:27amKristina

yeah well it just didnt work out
it happens to the best of us i guess
rushed into it
2:28amMe

Yea, and it makes for an expensive break-up, but u live and learn right?.. u always seemed like a sweet girl back in school

2:28amKristina

thanks bud
i was cool with most ppl
some i couldnt stand of course
but
yeah we didnt have a big wedding or anything
but theres one good thing about it all, is my son Dominic, I love him so much
2:29amMe

yea, i know wut u mean. i was in a relationship for 3 years and i got my daughter so it was well worth the BS i deal with now..

How old's your son?

2:29amKristina

yeah i think its mostly the age difference between us
2 1/2
3 in Aug
hes 39 and I will be 28
so I think thats what it is
idk
2:31amMe

my daughter just turned 3 in march.. yea, i see older guys being possessive but idk thats kinda a stereotype from the few i've seen

not personally hahaha

2:31amKristina

i know
no worries
i saw a pic of u and Heather
u guys tight?
2:31amMe

yea, that was fun. yea, shes a good friend of mine, wut about you 2?

2:32amKristina

we talk here and there
but havent hung out or anything, I think shes pretty cool chick
2:32amMe

shes pretty cool, not judgemental pretty open type of person

2:33amKristina

yeah i usually just say hi on fb
2:33amMe

so do u have your son most the time?

2:33amKristina

thats all
yeah well i have been sick for like 4 days
so hes been with daddy
i miss him
so ive been cleaning like crazy
i will have him next few nights
2:34amMe

that sucks but at least daddys still around, i have my daughter about 4 days a week

shes a big daddys girl

2:34amKristina

thats about the same for me
thats cool
how old is she
2:34amMe

3

2:35amKristina

sorry u already told me that
i must be tired
thats cool
2:35amMe

do u have your daughter saturday? i'm takin my friend out for his 21st

son sry

i'm tired too

2:35amKristina

actually
yes
but i have to work this wknd
we rotate wknds
so im on for this one
have fun for the big 21
2:36amMe

i worked the last 2, we do the same usually

2:36amKristina

yeah i cant wait for my vacation in July
2:36amMe

where u goin? florida's outta the question

2:36amKristina

so what do u do
oh
just chillin here i guess
with my boy
no big plans
but my friend from VA is coming up
VA Beach
so im excited
money is tight right now otherwise, yes, travel time for me
2:37amMe

i just quit my job of 3-4 years in construction, got a job at denny's and am working on getting my GED and going to college. no risk, no reward

2:37amKristina

good for u
i like dennys
which one?
2:38amMe

sucks now but hopefully it'll pay off, kindof a gamble. warrenton

2:38amKristina

oh
yeah well u have to take risks
sometimes
2:39amMe

Hey I got to get ready 4 bed, but I'd like to talk some more, give me your #.. I'll text u sometime

2:39amKristina

i would but i dont text
i know
im old school
my phone is so old is crazy
i have a i530 phone
will be updating soon
i barely get text for real
2:40amMe

haha well I'll call then, hang out sometime

2:40amKristina

lol
i know
yeah im about ready 2 go 2 bed myself
night owl these days
2:40amMe

me 2

2:40amKristina

i will hit u up on fb
im always on here for real
(like its going out of style)
2:41amMe

cool, i'll talk 2 ya then. have a goodnight

2:41amKristina

i work alot
so
you too, nice to chat with ya
ttyl

lol wow i felt like i was reading a boring novel. your werent different, fun or playful. it just seemed like you guys were catching up. you talk to much about her ex, you talked to much about ur ex, you werent playful or fun. just dull and boring. i mean next time have it be very playful and make her laugh. i dont rememberr a single lol or haha in her messages. girls put that when they are happy and laughing inside so try to make it more fun for her and not much of an interview. its a great rapport builder when you guys both have children.

I can def see your point! lol Thanks for pointing that out. Any articles you'd suggest on being playful and fun? I'm not real witty when it comes to crackin jokes. Unless I'm intoxicated then I'm alright. If the rest would have been on point, how was the # close? Was that about right?

lol i dont remember you getting the number....i just saw that you asked....lol and you cant have someone teach you to be fun and playful. just do whatever comes to mind, and even if it isnt fun or playful just try to make it that way. play games, like the cube, a ring routine, 5 questions, the question game. just anything to make her laugh and then tease her. i cant really teach you to be fun or playful, you just have to do it naturally. and the entire thing doesnt have to be playful, it would have been better if you just had some things where she laughed and was having a great time. but you just lead the convo to like interview style getting to know what happened since high school. and never try to talk about ex.'s.

*# close.. fail*. Yes I know. lol but the structure of it, was my question... Cool, I'm gonna check those games out, I'll also just try to entertain myself and see how it works. Either way, good practice.. But.. I'm learning flaws in my attempts that I didnt even know I had. Good things to know so I can iron them out. Thanks again.