Ok, some background first: I've been chatting with this hired gun for a while. She's probably in the HB8 range, but I really wasn't trying to game her because I get the whole hired gun challenge thing. Plus, she waitresses at a joint I attend that I use more to chill out and escape--I don't bring my boys there or dates. Anyway, I think my aloof attitude worked on her (though none of it was on purpose, I was really there just to have a few beers and be alone) because she asked me for my number a few weeks ago. We've texted a bit back and forth; mostly I've been funny and cute, but I haven't escalated since I'm playing the whole don't sh1t where you eat card--literally! I don't have AA and I can talk and joke with ease, my flaw is that I generally can't see the forest for the trees, meaning I have my head up my a$$ when it comes to gauging IOI.
So, last night I was at the restaurant, and we were flirting and the convo went something like:
Her: So, you have any plans for tonight?
Me: I'm looking for some people to come out and play since I'm playing hookey from work tomorrow cuz I'm going to the PHX Open.
Her: What's that?
Me: Really? You've lived here your whole life and you don't know what that is? You musn't get out often.
Her: No, I really don't know.
Me: It's a golf tournament in Scottsdale
Her: Well, of course I don't know it...I'm not old.
Me: Old? You have to be dead to not want to go. It's nothing but a huge party.
Ok, so I didn't invite her because I was going there to sarge, so that's not the problem. And, asking her to be my playmate wasn't in my mindset because she didn't get off of work until after 11 and I was looking to play long before that. My phone started blowing up and she kept asking, so who you playing with, boy or girl? I smiled and playfully said it was personal and when I was texting she came up behind me and saw I was texting a girl. And was like, "Oh, who's Kate?" After that I paid and was leaving and she basically followed me out the door, seemingly trying to qualify.
Now that I've bored everyone with my long winded story, the real question is: I took a picture of this dude at the Open who was in all white with a pink sweater wrapped around his neck and was thinking of sending it to her with something like "I totally rocked this pink sweater...I told you the Open's not for old people."
Would this be self-deprecating or just ball-busting/funny?