Speaking as someone who has had personal relationships with clients, I am here to tell you that it is indeed possible to date an escort. However, there are some rules on how to go about doing so.
First, you should remember that it is always up to the lady if she wants to date you outside of work. Just like in the regular world, you need to let the lady lead the situation.
Also, please don’t email or call an escort asking if you can date her. You would be just like EVERY other man in the world vying for her attention, plus it would be an insult for you to ask her to date you for free. Remember this is her job.
The best way to go about dating an escort is to start by actually booking her professionally. It is actually a lot easier for men to date this way because there are no strings attached and the fear of the lady pestering you to commit does not exist. This gives you time to actually get to know her as a person.
You should see her consistently (and be extremely generous) for at least 3-6 months before even asking her to date you. “Consistently” would mean seeing her at least once a week, or once every other week.
You should also take at least 3 trips together to see how you get on in the world. Studies have shown that the fastest way to learn about a person is to travel with them.
Book many overnights to see how you like sharing your bed with her. Don’t be afraid to have fun with her and explore different things together. Once you feel that your interests align, then go ahead and ask her.
If she says no, be respectful and accept it. Feel free to ask again in another 3 months because as with anything in life, persistence is key. Just be sure to not be creepy about it.
If she says yes, congratulations! But keep in mind that the real work begins. The same way you worked to get her, you will need to continue working to keep her. Every woman loves romance; take her on romantic getaways, send flowers, send gifts, get her spa days, etc, like you’ve hopefully been doing.
Ask her about her goals and help her achieve them. This one is very important. Helping a woman achieve her goals will more than likely earn you all sorts of cool points, not to mention that you would have a special place in her heart.
Also keep in mind that you would definitely need to support her financially if you expect her to give up her job for you. Always be honest about your feelings and never judge her for her profession. Remember you met her this way. The number one reason I decided to end things with a couple of clients I dated in the past is because they all of a sudden didn’t like that I’m an escort which is very hypocritical. The number 2 reason is because they expected me to stop working without them supporting me financially. If you have a great lady, you should always know that you would be spending a significant amount of money on her. That’s just life. If you have a problem with generosity, then dating an escort is definitely not for you.
Life is short; you should spend it enjoying each other and not worry so much about the unnecessary things. Trust your gut and always keep your word.