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Does anyone charge for multiple meet and greets?

I had a meet and greet with a dog owner a few weeks ago and it went well. He booked the housesitting stay and said he'd like me to come over again to get more familiar with the dogs, and I agreed. I reached out to him today to set something up, and he's asking me to come over for an hour one evening early next week, and maybe again later in the week. He lives out of my typical area so I'm already upcharging him for the booking, and I'm considering if I should charge him since he's asking me now to come for two hour-long visits before the actual booking instead of just once. I understand sometimes it takes a few visits for everyone to get comfortable with each other, but I'm not sure if I should lose money on another two hours, plus mileage, in one week if the booking is already confirmed. Should I charge as drop-in visits or consider them additional free meet and greets?

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The guy sounds a little creepy. Something does not "smell" right. Absolutely, charge for the drop in - or walk. Also, if you feel comfortable with the dogs tell him that, and if he says he still isn't comfortable - be very direct and ask, what is he uncomfortable with - exactly?

Thanks for your response! I agree it felt a bit off too. The booking didn't end up happening, which I think saved me some trouble in the long run. It was definitely a learning experience so I'm planning on charging "get to know you" visits after the initial meet and greet as drop-in visits.

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In this type of situation, it's reasonable to tell him sure, I'll be glad to do some drop in visits... and you could choose to tell him you'd waive the fee that normally applies to clients outside of your area.. Yes, it's great for the dogs to get used to a new sitter/walker and for you and the owner to get used to communicating with each other before a longer booking, but that doesn't mean you must provide all that for free. Ideally he can take advantage of that time by doing something locally (whether for work or leisure) while you're caring his dogs.

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Thanks for sharing your thoughts. It's helpful to know how other sitters handle these situations, and it's definitely given me some confidence to charge for these visits and avoid losing time and money!