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Joel
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So I have this acquaintance who I've always had a big crush on. He's never returned the flirting. I've recently found out that he's escorting. What would be a way that i could ask him to hire him without it turning awkward or weird. We aren't friends that hangout. Just acquaintances. friends of friends i guess. Thanks

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How did you find out he is escorting? Use the outlet he uses to advertise his escorting service to contact him as one more client. Of course introduce yourself and make sure he knows who you are, but as long as you respect the channel he established to deal with this business, everything should be fine.

So I have this acquaintance who I've always had a big crush on. He's never returned the flirting. I've recently found out that he's escorting. What would be a way that i could ask him to hire him without it turning awkward or weird. We aren't friends that hangout. Just acquaintances. friends of friends i guess. Thanks
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How did you find out he is escorting? Use the outlet he uses to advertise his escorting service to contact him as one more client. Of course introduce yourself and make sure he knows who you are, but as long as you respect the channel he established to deal with this business, everything should be fine.

of course i would contact him through RM. I just don't want it to be weird when we see each other the next time. or for him to tell his friends that i contacted him. But i REALLY want to hire him.

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How did you find out he is escorting? Use the outlet he uses to advertise his escorting service to contact him as one more client. Of course introduce yourself and make sure he knows who you are, but as long as you respect the channel he established to deal with this business, everything should be fine.

I agree with @latbear4blk. If he advertises, he is publicly available. Just hire him and take it from there. If he is a professional, he wouldn't brag to friends about your hiring him.

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of course i would contact him through RM. I just don't want it to be weird when we see each other the next time. or for him to tell his friends that i contacted him. But i REALLY want to hire him.

 

If you think you are not going to be comfortable afterwards, don't do it.

C'mon, just contact him in RM, tell him who you are and how happy you are to see him offering himself in the market. Tell him for how long you have been wanting to fuck him. If you don't want anyone else to know, ask him to be discrete, discretion is the middle name of most escorts.

I firmly believe in honesty and total disclosure.

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Put yourself in his shoes. You're now the escort. A guy has a crush on you but you don't feel the same way about him. You've never returned any flirtation that would encourage any future possibility. Now you find out that a client-contact you received was from this guy you didn't want to encourage. How would you feel?

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Now you find out that a client-contact you received was from this guy you didn't want to encourage.

This likely describes most of the escort's clients. Unlikely to be encouraged in the escort's private life but perfectly acceptable as a client.

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Put yourself in his shoes. You're now the escort. A guy has a crush on you but you don't feel the same way about him. You've never returned any flirtation that would encourage any future possibility. Now you find out that a client-contact you received was from this guy you didn't want to encourage. How would you feel?

 

Flattered, curious, and happy I am going to make some bucks.

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If the crush is irresistible, I would approach him in a neutral social setting, pulling him aside for a private word. "I've seen your escort advertising, and I'm sure you already know I'm interested. May I contact you as a client?" His comfort or discomfort should be apparent.

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He's advertising for gods sakes. That means it's ok to contact him. He also obviously needs the money so he will be grateful for a client.

 

It's not like you're contacting him on ok Cupid. You aren't asking to be bf you're responding to his ad saying I'd like to hire you.

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I was once contacted to do an overnight outcall with a client I had never met. I was confused as to why but when I walked into the room it turns out it was an acquaintance, and we had the most wonderful evening together and turned out to get along very well. Since we already knew the same people it actually made things easier. He wanted it to be a surprise.

 

One recommendation is assure him you are paying him and not pulling his leg, he may be confused if you decide to surprise him.

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