James - NO worries. Post your stuff dude.
Seriously. From that, you have wit. If you were able to deliver a playful neg mid-set, Hit a fun response to her "Victoria's Secret" comment... you're doing well.
Young? Yeah I get that. Were there undeniable IOIs? If not - I agree, I'd bail from sarging her - But I'd never stop conversing just as openly and freely. One train of thought I always get... "Hmmm 23, what's her mom look like? Maybe I can meet her mom?"
There's a kid my brother works with (engineering firm, this guy's an intern who was hired after graduation) who I built a great cocky rapport with... I saw him hugging this MILF one day and I started in on him...
me: Dude, who was the hottie?
him: Um that's my MOM
me: Cool, your mom's fucking hot. Can you introduce me?
him: No!
me: Why not? That's fucked up man, is she seeing anyone?
him: My dad
me: Cool... is it serious? I mean how long have they been going out?
him: They been married for 28 years!
me: So are they on the rocks? Do I have a shot? Work with me here.... hey - don't walk away!
.... Fast forward... The receptionist motions me over...
her: You're awful
me: Bullshit, I'm amazing. I've had myself... (wink).
her: (rolling her eyes) I know... your brother talks about you all the time.
me: Lies I tell you!... what'd he say?
her: That you're a player.
me: Ow that hurts.
her: Doubt that. But that boy is innocent, you can't say that to him?
me: Well, I can't take it back. I need to be punished now, huh?
her: You're so bad!
me: I thought we covered that.... so, when are you going to buy me a drink?
her: When my BF says I can
me: That's awesome, does he tell you when you have to pee, too?
her: OMG you did NOT just say that...
me: It happened, you should deal with it... seriously, when are we getting a drink?
her: Like I said I have a boyfriend... and
me: (cutting her off) Darlin, he's not invited. You are. Think about it. I'm going to bounce. I've got "player shit" to attend to...
Since then, my brother said she's questioned him about me more than once (I don't go to his office often). She has a BF, but she's obviously interested - I don't plan on acting on that... it's my brother's career and I don't fuck with that shit... but it's there - ALL because I was having fun with a dude....
I truly get a kick out of this shit!
RR