Toronto BBFS

Dating with an escort

So I ended up having bbfs with an escort and can potentially date her. And I am looking for your advice as well. Here's the story.

I'd like to share with what happened and ask for your comments and advice. Thanks in advance!

Without going into too much detail... I'm 21 years old and I've seen a 20 year old (2 months younger than me) girl at a classy agency who started her career 5 months ago when she couldn't find a co-op internship. To give you quick run-down of what happened... many times she complemented, said i was sweet, nice, etc. And said she likes me. Asked what she likes (as in in bed) and also said i like you! Nothing too surprising there, can happen. But interestingly, I she studies philosophy and i study political science (and have great interest in philosophy) - so we ended up discussing about Kant, Hegel, Nietzsche, Aristotle, etc for the entire session. She also asked what I'd like to do as career and when i said become an academic she reacted as so I'm preemptively fucking my professor! And she had crush on a prof before for a year. She also said she is a nerd herself and likes nerds. I have not met any escort so far who could discuss about the metaphysics of morals or anything of that sort, and i have not met any girl who was passionate about that stuff either! Anyone i knew found those classes boring!

But what happened next is the key thing. She was blowing me (and was curious about how Kant's metaphysics derived from geometry so asked me to explain while she's blowing me) - and after awhile she got rid of the condom and started bbbj even tho normally it was extra. And after awhile she said this is our secret ok? I thought she meant the free bbbj and wanted me to not mention it on review-boards so i nodded. And then she got on top and first she was grinding on me a bit so i thought it was it but then all of a sudden she inserted me inside of her. I was not expecting that and she definitely did not clearly and explicitly ask. So that's what she meant by "our secret." Hmm. And then maybe jokingly she said now tell me what you think about the ethics of lying. So we talked about the letter Kant wrote about not lying even if it may mean the death of someone and compared it with Hobbes' consequentialism whilst both deriving from rationality and not emotion etc. -- while she was grinding on me with me being inside her without a condom.

Overall, she seemed and sounded genuine and sincere - i could not sense any fakeness and i mean at least she can't really fake her passion and knowledge for philosophy. She wasn't the most amazing girl physically (tho she was still beautiful) or sex wise but talking to her was just on another level, it did not feel like just trying to pass the time by talking about general things. Even on the first session, i never wanted to stop talking to her and talking to her was the most fun thing and what i miss the most about her. I would have loved to have her as my girlfriend or even as a friend!

So I will for sure visit her again and see what happens but I feel like asking her out on a date, perhaps asking her phone number. I know, this should especially not even be attempted without being an actual regular and getting to know her but I'm in the city for only 2.5 more months. If anything, I'd love to get to know her a bit more and I simply don't have the funds to see her more than one or two and maybe three more times.

I'm not trying to go for a freebie and am even fine with just remaining as friends and I really don't want to make her feel like i am just seeking a freebie out of her and that i do not care about her but if i ask her out that's what she might think I'm afraid. And I'm also concerned about asking too early. And of course i am concerned about her not being interested in seeing me off-work. I'm just not sure what to do at all. But i also feel like i dont have much to lose by just asking. But even then, I'm not even sure what the best method to ask would be.

My personal opinion 99.9% of the women are looking for money only.She might be young,naive and new to this business but she will learn fast.You can't mix business with pleasure.Alot of people I knew learnt the hard way its best not to fall in love with an escort,stripper,masseuse etc.

Dude, I am only trying to help you here. I have a story almost exactly the same as yours. I am also a nerdy guy, so I completely understand how awesome this was for you. My advice is do not get emotionally attached to an escort in any way what so ever.

A quote from your post:
"and I really don't want to make her feel like i am just seeking a freebie out of her and that i do not care about her but if i ask her out that's what she might think I'm afraid"

This tells me you care (i.e. are developing an emotional attachment to her), which is understandable given the story you told. My advice is do not proceed down this path. It will not end well for you.

You are a nerd (Poly sci not math), but consider the mathematical probabilities:
1. That you will both fall in love with each other and live happily ever after: 0.00000000000001%
2. That she may care about you but it will still end very badly: 49.9%
3. That these girls are experts at this kind of thing and she is playing you like fiddle: 49.9%

It's a very confusing situation. I'm a lot older than you, so I have the benefit of experience. I'm currently seeing someone as both a friend and an escort. We've discussed several times the confusion this causes. She's also older so we're both at the point in our lives where we are able to speak frankly.

We keep it as friends and business, but are clear there cannot be any emotional expectations. Yeah, attachments can happen, but the foundation of your relationship is inherently unstable. Tread carefully.

For us, we’ve been doing more and more where we just hang out. But I’m also more than comfortable if we never have sex again or if she needs to move on and I never see her again.

Because of the weird situation, we worked it out that if we spend time and there’s no sex, then no money is exchanged. This is extremely unusual in terms of how matter of fact we are about discussing things. That takes maturity, experience, and to be honest, people who know themselves and are in agreement on what they want.

You run the risk of wanting more than she does. That’s never good. So here’s where I net out. If you can enjoy your time together, then that’s great. But going beyond that requires a very unusual situation and place in life.

I also think that while it may seem like a fairy tale, it isn't. Let us look down the rabbit hole if there is a relationship to be had from this. Don't you think that a relationship will be built on trust. This is where it will breakdown.

No. 1 - Will you trust her since she is an escort and will obviously be fucking other guys and also making out with them and establishing an emotional/physical connection?

No. 2 - Are you the jealous type? Will she quit for you and how will she support herself or you support her as she is used to standard of living

No. 3 - Can she trust you? You guys met as client and escort - can she trust you to not go and sleep around since once you get past the mental attraction, I believe you mentioned that she is not incredibly hot?

My 0.02

I appreciate all of the reponses, thanks! But to clarify, as I said, I'll be in the city for only about 2 or 2.5 more months. So, I'm not necessarily looking for a long-term relationship. If it turns out to be one, that's good but I mainly want to get to know her more. Aka. I'd like to date her or at least be friends. And I also am not the type of person who minds multi-relationships or having an active sex life. So in short, even just being friends or dating to get to know each other would still would mean meeting outside of the agency - and I'm asking for advice on when or how to ask her out, or if I should. After all, a refusal may mean I may not see her again even as business.

With all the warnings understood, ask her if she wants to meet outside the agency. Let her know that you’re leaving in a couple of months and would just like to enjoy more of each other. Make sure she understands you’re understanding if she says no.

Worst case in the short term is she says no. And that’s her perogative. When I’ve gotten to know escorts outside of their profession, it was after several visits and their volunteering interest. T

But they also knew I was not interested in anything serious. Like I’ve mentioned, blurring the lines between professional and personal is always tricky.

BAD IDEA. DO NOT DO IT.

DO NOT GET INVOLVED WITH HER.

I've been there -- done that.

NO NO NO NO NO. You hear?

To quote the philosopher W. Jennings,

‘be careful of something that’s just what you want it to be...’