I don't really have a problem being noticed by women or talking with women. I don't have much of a problem when it comes to approaching women either. But I've been noticing lately that when a woman makes a comment at me that I'd consider 'flirty', I am usually stumped at what to say. I suppose you could say I am not good at ad libbing conversations.

For example - Ordering food with friends, friends and I are joking, girl behind counter says 'you guys seem like fun', I say '...... yeah'. My brain just stops on encounters like this. How can I condition myself to react better to this sort of interaction?

Trial + Error man! every man since the dawn of time has felt like that at some point. It will take time but the best way to condition yourself is to sink or swim. just learn from your mistakes and keep this state of mind...."everything you say is the right thing to say" dont be afraid of failure...USE IT!

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Winning***always***

I've had similar problems in the past, and still do if I'm not in the right frame of mind. It's not that I'm shy, it's not that I'm intimidated by a good looking woman. I just simply don't think of things to say.

So trial and error isn't always the answer to this sort of thing, because how can you trial something when the problem is simply that you haven't got anything to trial? I do though think practice is the key. In every conversation you're in, and I'm talking even about moer comfortable settings, not just when you meet a girl for the first time, force yourself to be more talkative, to take more initiative and be more "off the cuff"... say the first things that pop into your head more often. If nothing pops into your head straight away, FORCE yourself to say SOMETHING more than one or two words long. It might come out ridiculous the first few times, but eventually you'll build on it and it will get better and easier.

Get better at that. Also listen to more people, watch TV shows where this sort of thing happens. You don't necessarily want a pre-packed "line" (you'd struggle to get one that fitted into every possible thing a woman might say to you), but you might get some better ideas of what sort of thing to say - and probably more importantly, how you should say it.

Yeah see that's the thing, I really don't have much to say. I'm introverted around people I don't know. Thankfully I don't have any issues with anxiety, or uneasiness around woman; It's the same way around guys too, I just feel extra dumb when a cute girl tries to pick a conversation with me and I don't even acknowledge it.

It's interesting that you say watch TV because, I don't watch TV at all. I work with computers, so I am not exposed to new people on a daily bases. I guess it's just a 'watch and learn' sort of 'learn from exposure' kind of thing, huh?

Practice conservation with people that dont interest you . random strangers guys girls old ladies. dont wait till it actually matters you dont have to watch tv there are a lot of things to talk about that are not current events. Food,music, travelling.If I were you I would have at least two conversation pieces. Like you know I have alwasy wanted to try this food _________ and then ask have you ever had it ? What is the weirdest thing you have ever put in your mouth(invitation for her to be funny) and then go from there .

I often don't have much to say either; perhaps I didn't make myself overly clear in the post above. But you have got to force yourself to say something. If you sit there thinking "oh shit, I've not got anything funny to say back", then you're not going to say anything back.

Don't try and THINK of something to say on the spot either. But force yourself to say something. Don't connect your brain. Just get your mouth and vocal chords working and say something. This probably doesn't make much sense, but you're not going to become better at talking and thinking up stuff off the cuff unless you practice it. Watching TV and comedy shows etc. help, it gives you a good framework of how to say things etc. But even so, you're going to have to work on it yourself to have it impact you. Don't worry about sounding silly at first - initially I quite often said things and then ended up just mixing my words and stopping mid-sentence! But eventually you get better at it.