Bingo! Women hate when men talk about themselves too much, so restrict yourself to answering direct questions on that level. Instead, ask her questions. I’m going to differ from the other advice here- find a topic that you know very little about but she’s interested in, then ask her to explain the topic to you. That leaves you tons of room to learn something interesting and get her talking about something she’s comfortable talking about and interested in. Come on, we all love explaining something exciting to us, right? Let her do that to you.
It must be repeated:
The key to good conversation is to ask questions.
That’s not to say you interrogate; you ask questions, and build on the answers.
Unless you’re online…then you can build a conversation out of, well, anything. You don’t even need to ask questions, just be completely batshit insane, and they’ll do the asking of questions. Not insane-stalker, but insane-witty. Just take whatever you’re given and, well, misunderstand it. Blow it up. If they say “I hate ants” you say “ants were spawned by the devil”, or “ants are just the cutest little buggers on the planet”. Then maybe go into a story about how you wish ants were 10 feet tall, so you can see 'em coming. Or so you can go for ant rides around your parent’s house. You can go anywhere from there 
That’ll keep 'em interested, if you can keep it up and mix in some real info.
Chat up every middle aged to old woman you meet, they love it. Try to hit mostly married women, with kids, and grandkids. Even the lamest possible conversational gambit, in any situation will work. Be nice, be humorous, polite, and ask a lot about what goes on around town. These women will not be your “target group” but don’t worry. Within a month of making friends with these women they will begin fixing you up with every available age appropriate woman they know. It’s a girl thing.
TrisDamn, my problem is that I can’t go up to the girl in the first place. Give me an opening, some sort of shared conversation opener (somebody doing something outrageous to comment on, waiting in line, anything simple I know I can relate on) and I can take it from there, but sit me in a party and tell me to introduce myself and I freeze, i practically need to carry around a pick to break the ice (figuratively speaking)
ETA: that might help you, actually, if you’re at a shared event, or there’s something happening to direct the conversation that way. “Are you here with people” “have you seen something like this before (followed up hopefully by you sharing a similar funny anecdote)” and try to get some sort of personal detail out of her that you can ask about.
That’s the best advice here.
Also very good advice, but for the wrong reason; it’s very good practise, and you might learn something that will impress a younger woman.
I disagree; I think statements are better. They’re less intrusive and demanding.
Horrible weather; this bus usually runs ten minutes late; I’ve just started her most recent book; the whole-wheat are very good here …
Under no circumstances, ever, on pain of death or permenant chastity, EVER try to start a conversation with ‘Good book?’ to someone who is reading.
I would just like to add that I’ve been happily married to the man of my dreams for 4.5 years. He is (by his own description) seriously affected by Social Anxiety Disorder. He is smokin’ hot. (He still looks like that, just with a few more gray hairs and a few more muscles.) A mutual friend set us up lo these many years ago. Our first few conversations were not easy, but they were sincere… he won me over (despite his conviction that he would NEVER be attractive to someone who found him attractive) by looking at, asking questions about, and really wanting to know my answers about, the books on my shelves.
</bragging> 
So, you weren’t reading at the time, right?
Funny you should ask… Not at that first moment, no (I was a bit distracted) though I might have wished I’d’ve been… but was so at many moments soon thereafter and since.
Why? 
I remember being single. I remember being interrupt at important points in good books by someone plopping down beside me to ask, ‘Good book?’.
Never occured to them that if it were a good book, I would prefer to read uninterrupted, or that if it were not I would not be so engrossed. Nope, they just saw an opening line, and took it.
Gits. Drove me nuts.
[OTOH, if someone waited until I came up for air to ask a quick, ‘That one any good?’, I would cheerfully talk for hours. Sometimes continue the conversation over breakfast.]
"no woman wakes up saying “God, I hope I don’t get swept off my feet today!.. any man has a chance to sweep any woman off her feet; he just needs the right broom.”
“Don’t be the guy in the PG-13 movie that everyones really hoping makes it happen…be the guy in the R movie you’re quite sure if you like yet.”
“Be kind of a dick…be David Carusso in Jade”
I’m not sure if you’re on the right message board for what you are asking. There are entire web sites dedicated to picking up women. Guys who all they do is go out and scientifically figure this stuff out.
Most of the advice here is good for boring some girl into submission. I’m ready to go to sleep just from reading it. Forget the stupid Q&A stuff. It sounds like you’re conducting an interview.
How you doin’?
Nava, engineer with boobies.
There was a bloke who once he’d got a girl,any girl, into his motor virtually every time he 'd end up having sex with her.
A less successful mate asked him the secret of his success and he pointed to a white circle painted on his dashboard,when the girl sees that she comments on how unusual it is and then we start talking about white things in general which brings us on to topics like virginity which leads on to sex in general and then we end up doing it instead of talking about it.
His mate thinking that its worth a try paints a white circle on his dash and then offers an attractive colleague a lift home from work.
As she sits down she notices the circle and says “Thats a very uncommon thing to see in a car”
“Yes it is isn’t it?
Fancy a fuck ?”
Brilliant! You win the Internet.
I am so bookmarking this thread.
Ah, engineering careers and boobies. One of the best examples of “two great things that go great together.”
Proposeth Zeriel, “two great things that go great together.”
New Tri-Bond question!
Cookies/milk, peanut butter/chocolate, engineer/boobies
Tsk Tsk, man boobies are not what people usually mean by boobies
Ooh, he looks like someone who gets hotter as he gets grayer (just like George Clooney. You can tell him I said that).
I always go straight for the bookshelf when I’m allowed to wander in someone;s home or apartment. Speaks volumes.
Nice turn o’ the phrase!
Thanks for your help, everyone!
30 y.o. student