Post: #1

Hi guys- longtime lurker, first time poster. I'm looking for some logistical help-

Background- I play poker a lot at a casino, a massage girl there was giving the guy next to me a massage and I chatted her up for a while, pretty flirty, the kid next to me getting the massage even said 'wow sounds like you two really like each other, you should ask her out'. Really dumb and awkward, I played it off. She's seen me there a lot before but I never get a massage from anyone ($2 a minute huge waste of money). So a couple weeks later she came by and we were talking a bit, she asks if I want one and presses me even as I say no, eventually agrees she's gonna take me out for a drink if I get one. So I get one, not actually expecting this as she's working and will say anything. But she comes by later and says so are you going to give me your number. So we were texting and I said I do tax consulting and she mentioned she got an IRS notice asking her to fill some form out for her 1040 (sexy texting, I know :/ ). This was after we agreed to meet up for a drink. So I tell her to bring the notice when we meet up tomorrow. Will follow up tomorrow afternoon on time and place to lock in- saw the logistic thread and non flake thread, great suggestion to prevent flaking.

So my question is what should I do for drinks and me helping her with this. Drinks first then suggest we go to my place and do it? Bc I'll need my laptop for it. But then we'll be pretty tipsy? But it's good plausible deniability for her to come to apartment after bar. Tell her to just come straight to my place and we'll do it first then go to lounge? Seems like a super lame way to start out, plus will be difficult to get her back into the apartment after we leave. Kind of a simple question but thanks for suggestions in advance!

Post: #2

Don't mix business and pleasure. She's a date not a client.

You've already told her to bring her form along, so you can't go back and "un-say" that, but what you can do is focus on making the date fun enough that taxes are the last thing on her mind. If she makes mention of it, you can tell her you'll help her with it, but not tonight. "Tonight we have fun."