I recently hired a guy to go away on vacation with me whom I had seen several times before. Lots of communication up until the trip, which was the most time we had spent together, and it seemed like a pleasurable time for both of us, and we agreed to do it again some time. However, afterwards in the several times I’ve reached out since then in a friendly manner, communication has been more distant than before the trip, with polite, but terse, and often slow responses until now no response at all. I wonder if I have misread his willingness and seeming encouragement to communicate between our times together. Should my only communication with a regular escort be to arrange time together and otherwise be silent? If I had been told that, I would respect that wish, realizing he’s not “on the clock,” but I now fear I have misread his friendliness and shouldn’t have responded in kind. Was it just to get some business? Or is the distancing a signal that he does not want me to hire him again? I am now questioning my judgment in what I thought was a beautiful time together and had hoped to do again. I am combing through it looking for signs that he was having an awful time with me to explain the distance towards me now. I would hate if it were something I had done.

It sounds like you genuinely enjoyed the time you spent together, and it’s understandable that you’re reflecting on the dynamic now that communication has shifted. Relationships with escorts can sometimes blur lines between professional and personal, especially when there’s genuine warmth and connection during your time together. However, it’s also important to remember that their friendliness is part of the service they provide, and they may have personal boundaries about communication outside of arrangements for work. The change in communication likely isn’t about you doing something “wrong” but more about him setting professional boundaries, either intentionally or because he’s managing his own time and energy. Escorts often interact with many clients and may choose to keep communication primarily focused on scheduling. To move forward and if you want to hire again, you could say something like: “Hi [Name], I just wanted to check in and see if you’re open to planning another trip or meeting sometime soon. If you’d prefer to keep our communication strictly about arrangements, I completely understand and will respect that.” This approach acknowledges his boundaries while keeping the door open for future interactions. It also signals that you respect his time and space, which is likely to be appreciated. If he doesn’t respond, it may be best to let it go and not take it personally. More than anything, try not to second-guess yourself or overanalyze the past. The connection you shared was genuine, but it’s important to remember that his distancing likely isn’t about something you did wrong. It’s more about his own preferences or boundaries, and that doesn’t diminish the value of the time you spent together. Focus on what made the experience special for you, rather than seeking definitive answers about his current behavior.