My older son was left with a friend for the first time at 2 1/2 and my younger one is 3 1/2 and has never been without dh or I. I'm sure if we had had family around they would have been left with them a bit, but our families are on the other coast and we don't really have the money for extra child care. Plus, I haven't ever really had the hankering to be away from them. There have been times, like for dentist appointments, that I wish it were easy to just call up our regular person and drop him (or them) off for a couple of hours. But when you don't have a regular person it seems easier to just make sure one of us can cover for the other.
Until recently I never felt like I needed any sort of date night thing. I don't exactly feel like I need it now, but for the last couple of months, I've been studying after the kids go to bed for a test that's still three weeks away. It has been fairly grueling and I haven't had almost any time with dh alone. Before studying, I was fine with us hanging out for the couple of hours after the kids went to sleep.
My older one did great when he started school, never cried or worried about us leaving. But my little one is more worried about where I am, like if he doesn't see me right away he gets a little freaked. And I tried a couple of times to leave him in the Y play area, which he thought looked like great fun, but he didn't want to be there without me. So, I'm a little worried about leaving him for preschool in september if we manage to come up with the money for it. His teacher would be a close friend of mine who he really likes, so my fingers are crossed...
eta: I am the only one I know IRL who doesn't use babysitters or other childcare almost ever, but I think I may also be one of the oldest of the moms I know. (I'm 42.) Dh and I had a long stretch of freedom before we had kids and I think we're both just more interested in being with the kids than going out and doing other stuff. A lot of my younger friends, I think, kind of have to work that stuff into their lives with their kids. My mom was 19 when I was born and had no money, so I wasn't with babysitters a whole lot when she wasn't working, but I was at all the parties with her and slept many nights under barroom tables with the children of her friends, which I actually remember as a great thing! So, while my friends look at me like I'm deprived for never getting out, I don't think that's quite right. I'm just at a different place.