My advice is to apply the same techniques you would when deep diving a girl to yourself. Talk about the whys, escalate positive threads and cut negative ones, focus on feelings over facts.
So if you work for a brokerage firm like I do, dont talk about the boring operational stuff you do. Instead I talk about how I've always been fascinated by money, and the concept that you can make money using nothing but other money. Or I talk about how I used to work for a small start up, and now work for a giant corporation, and both have their pros and con's. By the way what type of work environment does she prefer?
The key to almost any good conversation is talking about CONCEPTS and FEELINGS. The biggest mistake most guys make is being too factual. Even the most interesting topic can be boring if you talk about it in a bad way. And believe it or not, even a boring topic can be really interesting if you bring it up the right way. Ever resorted to talking about the weather? We all have at one point or another. And it sucks right? It typically sounds something like this:
"Sure has been warm around here lately for this time of year. I remember last year we had snow on the ground right now!"
Zzzzzzz... I got so bored writing that I couldn't even muster another sentence of example. Terrible right? That conversation is going nowhere. What if we talked about the weather though and I said something like this:
"Its crazy to me to think about weather. It makes you realize how big the world around you is. I got up this morning and checked the forecast and it said "pouring rain." and I realized that no matter what I did, thousands of gallons of water were going to pour from the sky. But at the same time it also shows the power of human ingenuity. I mean, the fact that someone out there can do some calculations on a computer and tell me that rain is gonna be a thing today is crazy! What an amazing world huh? Glad I brought an umbrella"
You see the difference? That second example has legs. We could talk for a long time in a lot of different directions on that, most of which have absolutely nothing to do with the fact that its currently raining. I simply took a fact (rain) and related it to some really interesting concepts.
Do the same thing when talking about yourself. No girl I've ever been on a date with had an opinion on the securities industry moving from T3 settlement to T2. But how intangible the concept of money is? Working for a big company vs a small one? These are CONCEPTS that anyone who has ever worked or had a credit card can think about and relate to.
drop frame while backtracking and explaining/rationalizing because im worried what i say sounds stupid to her.
The key to preventing this is confidence. Me? I'm fucking awesome. Its taken me a long time to realize this, but I've got it pretty well on lock now. When I go on a date with a girl I know there is a 100% chance she will enjoy it and like me, and probably a 75% chance she'll end up sleeping with me. Why would I worry about sounding dumb? I probably say things that would sound dumb coming from someone else. Hell, I probably say things that sound dumb when I say them. But because I'm awesome and confident I dont worry about that
If you haven't gotten to the level of success you need to in order to be this confident my advice to you is to pretend like you are a confident successful man and act the way you think such a man would act. It sounds really dumb but it truly works.
I still remember one of the first major objections I overcame back before Id really taken off with my seduction skills. I was with a girl in a nightclub in Australia and we were making out on a couch in the back. She stopped suddenly and told me "I shouldn't do this, I'm already seeing other guys." Without skipping a beat I said "Thats OK, I'm seeing other girls" and started making out with her again. Honestly, I wasn't at the time; it was more of an unfulfilled fantasy than a reality. But because I had in my mind how the person I wanted to be would act I was able to roll with it. Later on when we were about a year into a serious committed relationship she told me that was the moment that won her over, and I would have lost her if I hesitated. I fessed up to bullshitting and she couldn't believe it! I'd seemed so confident and sure of myself.
Anyway, thats just some of my thoughts. Hope it helps!
PS: Just in case it wasn't clear, the point I'm trying to make with the nightclub story is not that you should lie to girls (avoid that whenever possible) but rather that you can fake confidence even if you dont have the results to back it up yet.