So, in the past couple of days, no less than four super-hot single Moms have cropped up.  If I recall, my second SB was an ideal MILF...20, huge tits, nice shapely body.  Problem was she never stopped talking about the baby-sitter  LOL   I mean she could be in the middle of sucking my dick and seconds later mention she should call the sitter and see if everything was OK.  Obviously dumped her after the second meeting.
Just wondering, from you guys with more experience, what issues have come up and what did you do to solve them?

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leaves the child by itself.  My play would be to tell her you will pay the babysitter when you take her home.  Then you get a look at the sitter FIRST (essential in my book), and if you like what you see, hand her some folded over bills with your phone number on a scrap of paper inside where your lady can't see it.  Include a few words like "it would be fun to go out with you sometime.  Text me if you're interested".   Make sure when you pay her, she sees you peeling her money off of a very large wad of cash with some "blue" bills inside.  I did this once and it worked after my date told me her baby-sitter was a college girl.   I took her out to dinner one night.  She thought I was fun (hey, she was young, what does SHE know - lol), and then the next weekend we went on an overnighter to a beach resort.  Had a good time, but she was not a keeper.  Too inexperienced sexually.  

never considered that angle of it!
Just hoping the bbsiter is younger LOL

and never run into the same problem you had.  Otoh, I've had the Mom who had to get back home and had to cut things short because their own Mom was taking care of the kid and had run out of time.  I've also had a Mom with 2 kids who scheduled her dates to the minute, told me in advance exactly when she'd show up and when she'd have to leave.  That was ok with me.  And one amazingly cute SB I met recently actually brought her 9 month old with her to our coffee date.  She did not know how she was going to find time away from the baby to have BCD date with me and focus her attention on me.  Needless to say that BCD never happened.  I think if I had a Milf checking in with her babysitter constantly I'd be really turned off.  I'd probably dump her like you did.  For me, a big part of the fantasy in sugar dating is that when we are together my SB gives me 100% of her attention and makes me feel like I'm the most important person in her life.  That seems to work naturally with most of them.

Hmm, I've never had it occur that there was a baby in the wings, but younger than a certain age, having the kid in the crib or playpen wouldn't really bother me.  The kid has no idea what's going on at that age.  It's not like it would psychologically damage it.   Heck, I was the 3rd kid of 7.  Yet other than popping out babies, I had no evidence my parents ever had sex.  It's not that hard to hide it.

I am sure all of us have shown up to a session to find the provider with a VERY friendly dog that has to be put out of the room before the fun starts. Having an infant or toddler present really isn't much different, unless the kid is overly demanding or loud of course. Nothing is more distracting than trying to fuck while a screaming baby is having a fit. lol

 
That said, it's certainly not my preference to have more than just me and the object of my desire anywhere under the same roof during our time together, but it's not like having her 14 year old son in the next room, now THAT would be creepy.  

 
Lastly, I only feel this way about dates that are purely physical. I have ZERO interest in spending the entire evening, or even a couple of hours with an SB who has her child with her, but if the "date" is nothing more than a hook up it really doesn't bother me much. Come to think of it about ten years ago I had a "maid", actually a girl I met at a M&G who had thought about becoming an escort, but decided the life was not for her, but for some reason didn't mind fucking me for money. lol AAR she would come over usually late at night with her kid who was only a toddler, she would clean my house and then hop in bed with me and "clean my pipes" while her kid would be entertained by watching cartoons in the other room. I think we saw each other for well over a year to both of our benefits, and half the time I'd never get out of bed at all. She'd let herself in, do her thing and then let herself out while I'd just roll over and go to sleep after she'd leave with an empty sack and a clean house. lol

Its better than a dog because the infant won't sneak up behind you and lick your notes.