Sitter accepted my upcoming sit back in May. The sit is coming very soon so I reached out to inquire about her travel in order to plan the handoff.
She stated that she had not booked air travel yet. This was a bit alarming due to the closeness of the dates. She then proceeded to ask if her boyfriend could come along because “he has finally decided to go on sits with her”
Is this normal? This is my longest sit to date which already makes me a bit nervous, now this.
What are your thoughts?
Be happy for her.
Life happens. It seems you selected a young single sitter back in May. Young people don’t often stay single forever, so this should not come that unexpected.
You are lucky that she is still willing to do the sit. And it seems she asked nicely.
It’s not unheard of, but it’s entirely up to you if he comes. Ask for a bit more information about him. How soon is the sit? I always book my flights as soon as an overseas sit is confirmed. Last minute flights are always more expensive.
@legendvictoria
When exactly does the sit start?
I’d be very concerned the flights aren’t booked as yet.
I don’t understand how some sitters think its perfectly fine for a confirmed sitter to spring it on a homeowner after confirming a sit, they want to bring someone along on the sit. Its a vey uncomfatable postition to be in. (Speaking from experience).
If I am flying to a sit, I book my airline as soon as I have accepted the sit.
If the sitter agreed to your sit in May, but has not made flight arrangements yet, I would wonder why.
Her asking if her boyfriend could accompany her on the sit sounds contingent on her buying her airline tickets:
How do you feel about the boyfriend joining her?
Even though the sitter asked your permission for her boyfriend to accompany her, your agreement for the sit was for her only and-- did not include the boyfriend.
Just because her boyfriend “has finally decided to go on sits with her” should not make you feel obligated to that arrangement. If you feel uncomfortable with her boyfriend joining her, you are well within your right to say ‘no’.
@Chrissie Thank you for your feedback!
The sit is in 14 days. The flight is not international but cost definitely increases the closer the purchase is to the travel date.
In your place, I’d be kind of annoyed that she didn’t reach out earlier, but I’d give them a chance and go in with an open mind. I’d ask to schedule a video chat with both of them asap, which shouldn’t be too much to ask and hopefully will give you peace of mind. If you’re not okay with it you can say no, but at risk of losing your sitter. I’d say it’s worth considering, and might be a win-win.
@sharondc Thank you for your feedback!
I book flights as early as possible as well.
I guess my issue isn’t so much that she wants to bring her bf but with the timing of it. I reached out 3 days ago to inquire about her travel arrangements and her response was about the bf. Seems like she would have reached out as soon as she knew he wanted to join her.
This is a VERY important (long) trip. I expressed the significance/importance of this trip when we met and that I needed her to be sure before she confirmed.
I just hope everything goes smooth🤞🏾
@Shafofo Thank you for your feedback!
I like the idea of a second video chat. This one with BOTH parties.
@Manunited Thank you for your feedback!
I am very concerned that the flights aren’t booked. The sit is in 2 weeks. Maybe if the boyfriend comes, they will drive instead…who knows.
This is an extremely uncomfortable position to be in. I feel like I don’t have a choice but to say yes or run the risk of her canceling the sit last minute.
This is a very important trip. If not, I wouldn’t feel so backed in a corner.
14 days away and she hasn’t booked flights? 
@belluca My thoughts exactly! I’m trying to stay positive but my spidey senses are tingling like crazy!!!
I would be concerned that flights haven’t yet been booked, and would initiate an open conversation to express your concern and to try to find out why, and when she intends to book them. It would set you off on the wrong foot to start issuing what might be seen as ultimatums, but at the same time, you do need to have a cut off point, whereby you decide that if flights haven’t been booked she’s obviously not serious about doing the sit, and you will re-list and try to find someone else.
Re the boyfriend, at least she has asked your permission in advance, and, depending on the nature of the sit and responsibilities involved, I guess it could be beneficial to have a couple rather than one person? If you meet him on a video call and ask to see some form of ID then you will know pretty much the same about him as you know about her! Yes, she may have some good reviews via THS, but at the end of the day these are strangers who you are inviting into your home to care for your pets - you need to feel comfortable with the situation. If you’re not, then don’t hesitate to make alternative arrangements.
I like the idea that @Shafofo suggested of having a video chat with the sitter and boyfriend, particularly if you agreed that he can join her.
Since the sit is only 14 days away, I suggest reaching out again to the sitter and ascertain if she has booked her flight. Time is of the essence. Flights go quickly and prices increase with each passing day.
Hoping everything goes smooth and things actually going smooth sounds too uncertain.
If the sitter is showing this lack of organization by not booking her flight within 14 days of the sit, how organized will she be with your pets?
I have a sit coming up in two weeks. I have not booked my transportation yet. There are some different possibilities. But I am pretty sure that I will be there in time.
Anyway, the owners and I have been in touch a few times since May.
There isn’t the same level of easy/cheap flights in the US as in Europe (OP is in Arizona)
Ultimately it’s all about expectation. If the local flights can be booked at anytime then no great shakes (as long as that’s what you agreed). As for the BF, that’s annoying if you’re now in a tight spot and don’t want to lose the sitter. Just go with your gut feeling on whether it’s a yes, life changes. Do the video call & get them to lock in transport arrangements asap so that you can all relax. If it’s not a fit or you feel coerced then cancel them (for valid reasons) & go for plan b or c. #fingerscrossed
Why not?
Pretty sure and sure aren’t the same.
There is always a risk that if you wait too long, you may not be going anywhere–regardless of how many times you have communicated with the owners.
Booking transportation is no guarantee.
Anyway, it is just 900 kilometers. Two weeks is more than enough time to get there.
More reason to book sooner than later to allot for a backup plan