After some particularly weird flirting instances recently (and ones where I did not reject by asking for payment, I may add), I have decided to compile a mostly scattered list of ideas on how to best flirt with and ask a sex worker for a (free) date. It is probably important to also point out that this is really just a list about how to flirt with me and ask me on a date, and likely doesn't apply to all sex workers. I am a bit unique in this field, as a married polyamorous individual who doesn't ever limit the amount of people I'm dating. My social calendar is a constant balancing act, and one I have yet to master.
Enough asides, here are my tips:
- The most important thing to always remember when talking to any sex worker in any social setting is that sex work is work. It is my career, my profession, my job. In my somewhat unique case, it is also a hobby. But for me there is actually quite a big difference between dating people professionally and dating people recreationally. If you are confused about how that can be possible, ask me how I view the differences. But don't make assumptions about how I view my work, or how seriously I do or don't take it.
- Don't ask me on a date by saying you'd like to talk about my work with me because you find it fascinating or interesting. I love to talk about my work, and it will likely come up often if we're on a date, but I don't want to go on a date with someone just to educate them about my work.
- Don't make a joke about needing to pay me in order to talk to me. It feels really awkward.
- If you are unclear about whether or not I'd be willing to date you for "free" (for lack of a better term), please ask in a kind way. This is also awkward but I'd much rather get it out of the way.
- Do ask me about my interests, my projects, my passions, etc.
- Don't tell me you're more worthy of a date than others because you have awesome genitalia, you're going to "rock my world," because you'd "take care of me," or other similarly gross comments you might not ever use to come on to someone who isn't a sex worker.
- I am much more likely to date someone who is already in my social circle than someone I don't know at all. I'm not saying you should try to insert yourself into my social circle in order to date me, unless it's something that happens naturally. I am just saying to be aware of that when approaching me.
- Have respect for my time. Don't expect me to go a date with you tomorrow- it could be weeks or months until I can make it happen.
- Do let me know of your interest in a low pressure way, and then allow me to approach you for a date if I want it. I will if I am also interested.
- Do treat me as you would treat any other person you want to date.
In closing, I am going to borrow some words of wisdom from the person who most recently successfully flirted with me and dated me. For those of you curious how it happened: we've known each other for about 5ish years and I had a crush on him the whole time. Recently, he had a long-term monogamous relationship come to an end, and after some time spent healing he told our mutual friend that he had a crush on me too. Emails and dates ensued after that. His advice (it is very similar to mine, but is a great TL:DR summary):
I suppose my simplest rule would be: follow all the same rules you always follow. Dating a sex worker is like dating not a sex worker. If you wouldn’t say something while flirting with a lawyer, chef, construction worker, chiropractor, or accountant - don’t say it to a sex worker.