I personally do not like having the "what do you do" interview with people since it feels kind of like, well, an interview.

I would read the news headlines, listen to npr, or something similar to have subjects to talk about that aren't about either one of you specifically. If something funny happens to you that day at work, remember it and tell her.

Jobs, opinions, beliefs etc. will be naturally discussed within the context of other things and it will feel more natural.

ask the other person about themselves... you can start with the usual "what do you do for a living" kinda thing. but then get them to talk about how they feel about it. like "was this something you always wanted to start a career in?" then they will begin talking from their heart...things will def. move on from there.

Ask her "what was the best thing that happened to you today" or the funniest thing, or the weirdest thing.

All you really need to do is ask follow-up questions and smile, the best conversationalists rarely say much.

travel my dear, talk to her about where she's been in this world. If she hasn't been anywhere then talk about food and wine, what she likes to eat and what she likes to drink. See if she is a foodie? Then go on to music. See if she is a rock chic? Avoid what do you want to do with your life because it puts a lot of people off (it doesn't put me off completely but i know a lot of girls don't like it).

people seem to love to talk about themselves (especially girls) so dear's advice is great. when in doubt just ask her a question about herself!

If all else fails, order a glass of wine or two, it will open you up!!! But dont go further than that!

Compliment her on her outfit, ask about how she is nowadays and basically inquire after her. Like, "Anything interesting happened today?"

However, pay attention to her mood that day. You also have to alter your conversation according to her personality.

DON'T EXPECT TO GET LAID ON YOUR FIRST DATE AND DON'T EVEN TRY TO GO THERE... especially if you really like this chick! Making your date laugh is a good thing to be doing.

andaman, well said. A little blunt, but you know. it had to be said.

As a man telling another man how to start a convo..and ur asking DS this!! Come on!!!!!!! Your a man and you should know..sigh i'm disappointed...lol j/k
Anyways, just do the casual questions, Favorite movies, favorite things to do. Remember this, when she is talking, never ever interrupt her and be patient with what u want to say and if you are honest with her, the convo will be much much genuine and gives love that.

Man telling this to him is making want to go on a date now...man i need a gf.

Good advice andaman.

Asking questions is great advice and often leads into other areas of conversation. Ask favorite movies, favorite bands; when she mentions a girlfriend (and she most likely will) ask about the friend, how they know each other, etc. Just go with the flow once things get rolling. And hopefully, she will ask you some questions too, making you feel like she's interested in you!

i've never had trouble talking (maybe the opposite, lol) but just noticing what is going on around you and relating it to her. the beautiful day, would be a great day to go hiking or biking (what ever you like) does she like that? if you go to dinner about the things you cook, countries you;ve visited with intersting food, ordering the wrong thing when you didn't understand the language as well as you thought you did. i never liked a lot specific questions early on, too forced. a few general questions and you telling things too make it flow more. have fun

my absolute favorite is

" so tell me something about yourself that I don't know "

that gives them the opportunity to share things about themselves OUTSIDE the usual movies blah blah blah. Those questions are always asked so responding can get boring. Then hopefully he'll respond and you can go back and forth! Generally bringing up cool stories.

there's my two cents!