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It depends on what kind of mood my son is in. If he's playing and having a good time, he could care less if I'm there or not. If he has been clingy that day, I have to sneak out, pry him off of me, or get the babysitter (nana & grandpa or my sister or his nanny) to distract him and take him to another part of the house so I can leave.

It's rare for us to use a babysitter while LO is awake (5.5 yrs old now). We tend to have friends come over and do a watch-the-kid swap after bedtime in order to go out and not pay $$.
However, when LO does have a babysitter she is always really excited about it. We kind of play up that we're doing something boring and she gets to play, or hype up whatever special thing there might be for them to do.
Sitters are usually the parents of her friends so she's familiar with them. We had a brand-new first time meeting her (for me and for LO) sitter while on vacation for a wedding and she did just the same as familiar people. Wanted to chat and play, show her all the toys. I was surprised it didn't take her any time to warm up and I don't know if this would be the same every time but I was happy!

My 6 year old gets upset whenever we announce we have a babysitter coming over to the point where it almost makes it not worth going (1.5 year old is just fine). We’ve tried not announcing until right before but usually one of us slips and we’ll talk about what time the reservation is, etc. and he gets upset. The babysitters are usually former daycare teachers who have been babysitting him for years and yet we still get that reaction (though he’s happy if it’s his grandparents watching him). We’ve started letting him have movie night with the sitter, which involves ordering pizza and picking out a treat and that has helped a little. I hate that he makes us feel so guilty for going out but we likely have the issue because we go out too infrequently. Between the hassle of booking a sitter, the cost, and my son’s guilt trips, I always debate whether I should have stayed home!

@josina: I know, it sucks! DH was really surprised the daycare teacher was so honest about how LO was doing. You’d think LO would be used to other people besides me since he goes to daycare, but I guess being at home equates to mommy. So far the new sitter says it’s going well.

I should note that my son was in daycare since 6 months old so it's not like he is not used to being in the care of other people. There's just something about his parents not being home on a weekend evening/afternoon and having fun without him that gets under his skin.

My son was never great with care other than me, even though we exposed him to a nanny beginning at 4 months old, so I do think part of it is personality.

Now, he's more receptive, but we have my parents so we leverage them.

DS (2.5y) stays home with Grandma & Papa, so he is only used to 4 caregivers.

He was fine with our temporary full-time babysitter age 3-4 months. After that, with sporadic monthly babysitting with the same person, he cried every time and was fussy up until age 2. After age 2 he has been better, but more disobedient / prone to conflict with other kids, sooooo babysitting is still hard and we don't ask for it that often.

We don't do paid babysitters, just babysitting trades.

@Shantuck: this is us!