Why am I such a bore?!!

I remember when I was 14 or 15, I could chat with girls for hours and keep them engaged. but now, I suck at chatting with them online to attract them. following chat is from a dating site, where I started to talking to a girl, but it didn't really go anywhere.... please help


me: Are you the type of person who can accept a sincere compliment?
her: like?
me: you have a beautiful smile
me: your turn :P
her: thank you
her: happen to see you live in boston and im not looking to do an "online boyfriend"
me: same here, I really don't want an "online gf" but I am planning to move back to houston in december
me: would you like to get to know me online until then?
her: sure
her: are you from houston?
me: yes originally I am, I went to boston for college
her: ohh ok
her: thats pretty cool, what part of houston are you from?
me: I live in the north side, by the spring area
me: how about you?
her: katy
me: hmm... do you go to katy mall a lot??
me: *** Kissing ***
me: oops
me: i did not mean to do that lol
her: lol oh wow...and no i dont that mall sucks
me: haha i went there about 5 yrs ago, it was ok...
me: i noticed from your profile
me: that you're quite shy as well
her: lol yeah i can be pretty shy mainly around alot of ppl i dont know
me: same here... this is why I'm trying to get to know people online before I meet them
me: so let me ask you something
her: okay
me: If I were to see you on the street or the library or somewhere else
me: how would I need to approach you?
her: that ALL depends on where and what im doing
me: ok let's say you're at the library surfing the web and I notice you
me: and I really want to talk to you
her: ask about whatever it is im looking at or if you need help with the web ask for that
me: lol
me: wouldn't that be weird though??
her: no, im pretty use to guys hitting on me and hate it when the first words out of their mouth is how pretty i look, im more than just looks
me: thats true... but what if a guy just came to you and said "you seem interesting, I just wanted to introduce myself to you"
me: do you think a Direct Approach like this is better
me: or something more indirect
her: why are you asking all this?
me: well, honestly, I am very very shy around women... and I wanted a female opinion on this
me: I don't always want to rely on the internet to get to know someone
me: and you seem like down to earth, so I thought, I'd ask you
her: my opininon is to start smell talk about something you know shes into or likes
me: oh ok , I'll try that
me: so tell me more about yourself
her: what would you like to know?
me: I noticed, you like photography... are you taking classes for that or just learning it independently
her: no classes yet but soon
me: i have always wanted to learn more about that, being an engineer we learned the technicalities of it
me: but it must be amazing to actually have a career in that field
her: it will be yes, i love it and learning about it so its gonna be pretty awesome
me: so was it always your dream to become a photographer or did you change along the way as you grew older
her: its pretty much been something i wanted to do
me: well that's nice, I'm very happy for you!
me: I gtg meet friends for dinner, but you seem really cool and I would love to get to know you some more
her: okay bye have fun
me: bye

Look for things that don't matter, but tell you about her.

-What's your favorite color?
-If you could be any animal, what would it be, and why?
-If you get lost in an unknown city, do you stop and try to figure out where you are or do you keep driving until you find something familiar?*
-What's your dream car?
-If you could have an exotic pet, what would you get? Compare to the animal they want to be.
-If I gave you $100 and told you you have to spend it on all on an item or items, what would you buy? What if I said you had to spend it on an experience? What about if I gave you $1,000?


I can talk to anyone for at least 30 minutes based on the first two questions. The key is to follow-up on the responses.

*From here, I might go into a funny story about getting lost and driving around on a sidewalk in the center of an outdoor mall.

Some questions that may be good, but need to be used after gaining some initial intel are:
-If you had a baby, what would you name it? Girl name and boy name.
-Have you ever been to a drag show? What did you think of it/where did you go? OR Would you be interested in going to one? You can follow that up with: I have a friend who does a killer Celine Dion show. Maybe, if you don't turn out ot be a creeper, I'll let you go with me sometime.
-What's the most embarassing thing that has happened to you that was your fault? and not your fault?
-If you had to move, where would you go, and why?