If I may tell a truth... the older he gets the harder it gets. I'm thinking "When he gets older" really means "When he's 18 and on his way to college."
My 3.5 year old child is:
No flames here, but we chose to parent our child in a very scheduled manner. From eating to sleeping, we have a schedule for just about everything we do. Are we flexible? Of course. Now that Jack is getting older, he is able to voice when he is thirsty or hungry so waiting until a "scheduled" time to eat seems a little cruel and unusual not to mention, there are just nights when he is most definitely not tired at 7:30pm.
One of the hardest things for us to do is let someone do it for us. I finally talked my husband into going on a real date night. One where we go to dinner and a movie at a normal date time (like... not the middle of the afternoon), stay out late and drink a ton. Despite 3.5 years of her begging, he wouldn't bend on letting his mom babysit. I haven't the slightest clue what his hangup was, but I was finally over it. We were going out. Thrilled to pieces that I asked her after all this time, my mother-in-law broke land speed records to get to our house that afternoon. I made a bet with my cranky/anxious husband that she would get Jack to sleep without any issues (or should I say issues outside of the normal 3 year old anti going to bed issues). I dragged my nervous husband out the door so we could make it to our dinner reservations on time. Smartly, he ordered a scotch when we got there. He eventually calmed down enough to enjoy my wifely company and we proceeded to have one of the BEST movie experiences ever. I don't think there are many of these movie theaters out there, but if you are ever able to buy VIP movie tickets at a Paragon Odyssey theater, I highly recommend it. Around 8:15p, we got a text from mother-in-law: "He is sound asleep." Immediate relief shown in my dear husband's face. We even sat down for a couple drinks after the movie.
It was one of the BEST date nights we have had in a very long time. Our marriage ached for it and needed it.
While we don't consider ourselves helicopter parents, we do have some trust issues when it comes to leaving our son with other people. Yes that includes family. Mostly it has to do with breaking the schedule and the reprogramming we have to do to get back to our daily routine. After my sister-in-law settled down to get married and start her own family over the last year and a half, we lost our go-to babysitter and admittedly were kind of lost. We often drop him at my parent's house but that typically means an early night out and certainly very little booze (yeah... hubs and I like our liquor). Having his mom babysit for us was a big step. And guess what? Jack is still alive. MIL is happy to have her new babysitter status. It's a small step towards hopefully bigger things (OVERNIGHT date maybe?? Dare to dream...).
We confess. We are a work in progress. Stay tuned... I have a post forthcoming about our summer trip to Disney. If you thought trusting a new babysitter was hard, try the stress of bringing our preschooler on a plane for the first time...