It’s quite right what Colin is writing. We need to decline most invitations, whether we already know the HO or not, and I suspect most experienced sitters will have to do the same. Some HOs ask us back only once and then stop, others ask us for years even though we have had to decline half a dozen invitations from them already (which makes us sad since we really would like to help out and meet the pets+HO again, but often it’s just too expensive for us or the distance is too great).
Sitters here. I believe we have been asked back to all our sits bar one, and in every case, with 2 exceptions, we have had to sadly decline as we have already been booked. Often we have been asked back on 2 or 3 occasions. In our case we are usually booked up a year or so in advance to being asked back so even when a sit is 3 or 4 months away, we have been unable to help. Your previous sitter may well be in that situation. Conversely, the last home owner we sat for was hopeful that we could sit for her again as she found the process of vetting and interviewing sitters long and stressful and would be thrilled if she didn’t have to go through that process again
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We’ve once been on the other side of the coin. We were accepted for a housesit, and then 6 weeks before the sit, the HO canceled because their previous housesitters became available and the HO rather wanted to go with them. It was our first housesit as part of a long tour, so that one threw us and hurt a little! But of course we found something else and it turned out absolutely fine.
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Congrats @toml for ‘all this repeat business’ as being asked back is truly a great compliment!
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That’s sad and shouldn’t be a reason for cancellation, but good that you found sth else.
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Look at this in another way. If your phenomenal sitter sees that you have listed your sitting without contacting her, she will feel a little put out. Then, if you don’t like any new applications and you then return to her, she will feel even more peeved!
I think that you already have your answer from all of the responses above - just ask her back!!
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That’s absolutely awful of them. I would never do that. Once I’ve committed to someone that’s it. Unless something truly unforseen happens like the trip is cancled for reasons out of our control (which has happened once, when the cruise company we booked with declared bankruptcy and liquidated soon thereafter. But even then we scrabled to arrange a different trip and it didn’t impact our sitter in any way).
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Quick update: Thanks for all the helpful advice. Last night we asked her back and she is not booked during that time, and she definitely wants to return. Her mother is having surgery later this year and it isn’t scheduled yet, so while she is very interested in coming back she will let us know by the end of July or early August whether she is available after her mother’s convalescence.
This is fine, because I’m arranging everything well in advance and have ample time to set up another sitter if it doesn’t pan out.
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As the old saying goes, “if it ain’t broken, don’t fix it!” No brainer go with your tried and true
Hi @Zeke. A warm welcome to TrustedHousesitters and to our wonderful community forum. Thanks for joining the conversation 
Thank you certainly appreciate this service
This is great to hear.
Communication demonstrated very well between all parties 
I wouldn’t overthink this…If you found a “phenomenal sitter”, ask them back. Great and available sitters are truly hard to find. I had one sitter do a sit for me in Feb 21, July 21, and Aug 21
I have one sitter that has sat for me three times in the last year and a half. Things work so well that I’ll coordinate my travel with her availability. When I don’t have flexibility I find a different sitter. I like very much the possibility of working with the same people over time.
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We don’t like short sits very much, we feel we don’t get to know the furries very well.
However if we’ve been before a short sit is ok.
We did a three week sit last year that I had to work very hard with one of the cats on. At the end of the summer they asked us back for a long weekend. We went because I didn’t want that cat with new people for a few days!
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As a homeowner, I always contact my past sitters first after I’ve put up my dates, to see if they want to come back. It is easy for me and it’s nice to have someone come back who already knows my cat. Even more so for you as your dog will be happy to see a “friend” again.
If the wonderful sitter isn’t available then do approach new people but personally I always start wtih someone I know. I had a text recently from a past sitter who asked if I’m going away at all as he’d love to come back and on that basis I’m arranging a weekend away over the summer. It’s a nice two way arrangement when you can make it work.
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I would say if you, and your pet, are really happy with your sitter then ask them back by all means. Why wouldn’t an owner stick with someone they trust ?
We’ve a handful of repeat ‘clients’ now that often come back to us ( the last two invited us back for a subsequent sit the day after we left the first).
However we feel awful if we have to decline a sit due to other commitments or bookings. We just have to explain that we have multiple calls on our time and cannot meet all requests. Worse still, we then worry that, if someone else steps in, we might lose contact with some of our favourites 
I wouldn’t be concerned about losing contact with some of your favourites. We have just returned from a sitting where we last sat for the HOs 10 years ago.
The house, town, cat and dog had all changed but the HOs were just as welcoming, if not more!
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Quick update. She accepted our invitation to come back in February!!!
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It certainly is a compliment to be invited back. We had two great sits in Mallorca, looking after a couple of elderly Alsatians. Neither died on our watch but the owners now have no pets but still keep in touch and want us to visit while they are still home. Now that’s a success story! When it works it really works!
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