Something I've done in the past is talk about how awkward I was 1-2 years ago, and how crap my social life used to be

I don't know why yet, but it seems to get emotional rapport going with them and also acts as a DHV -brave enough to be open and honest-

Your thoughts gentlemen...

Don't use the word crappy.. rather say something like this:
"I gotta tell you a secret... X years ago I was a rather shy guy"

I did it once...

I was talking to a girl from college...she was totally into me.

So I told her...

"In my freshman year I did'nt knew a lot of people...no one from college celebreted my birthday cause It was on the first day of classes...so I did'nt knew anybody...that kind of sucked"

She stared at me with a WTF look in her eyes.

I had a lot of value in her mind...but I did'nt hold that much value for myself. A calibration mistake.

Try to make it like you were advertising a weight loss product. My life improved cause..yadayada I used to be really shy but I've learned since that...blahblah"

Redmole thats exactly how I do it, it helps with emotional rapport, if she feels sympathy for you then gets brought to an emotional high when she realises things turned out cool for you. Then it's good to go.