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Posted

so there's this guy that has hit me up on grindr a few times but our timing never worked up for a hookup. i see he offers services as i was looking for a massage? is it cool or not cool to hit him up asking for a service?

Posted

I would be careful as you proceed.  I think this could get tricky.

You say you've been chatting on Grindr - presumably for a casual non-payment-involved hookup - but your timing never works.  If you offer to book him and he's suddenly readily available to meet, it's a natural reaction to think he only has time for you if you're paying.  Maybe that won't happen, but be prepared for how you might process that emotionally.  Also, you might book him and have a great time but from there on are you going to go back to trying to connect for a "free" hookup or are you always expected to book a paying session?

Posted

Don’t overthink it. Just book him if you want to try him. You don’t say how you saw he was offering services though? I assume he wasn’t advertising on Grindr (they don’t like you soliciting for work on their app). Book him via his massage services profile, wherever that is, rather than via Grindr. 

Posted
On 4/27/2025 at 6:37 PM, Jamie21 said:

Book him via his massage services profile, wherever that is, rather than via Grindr. 

Agree. We pay attention to clients booking us through the normal channels. You don’t have to say anything about the Grindr communication. You want his time and service, which is valuable to you and to him. You get priority and the privilege of seeing him when you want to and receive the service you want. That’s worth paying for.

As far as the hookup is concerned, you may or may not ever meet him, and certainly not on your preferred schedule and not with the expectation that he is going to provide a service he normally charges for at the level of quality he would for a client.

Posted
On 4/26/2025 at 11:33 PM, jsr4022 said:

so there's this guy that has hit me up on grindr a few times but our timing never worked up for a hookup. i see he offers services as i was looking for a massage? is it cool or not cool to hit him up asking for a service?

I wonder if that's why you never were able to get together through grindr as well. He might have had massage appts come up.

Posted
On 4/26/2025 at 11:33 PM, jsr4022 said:

so there's this guy that has hit me up on grindr a few times but our timing never worked up for a hookup. i see he offers services as i was looking for a massage? is it cool or not cool to hit him up asking for a service?

In essence it's fine, but that's not permission to be fully trusting. Always caution. A good strategy is to as questions about setting, what exactly is he offering, location, etc. I'd treat it the same way that I deal with a hookup with a hidden agenda of wanting money. The app is just the means. The cyberspace is no different than the rest of the world. full of scammers, hustlers, and good and bad people.

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