My wife and I are bumping into our 50s, but have been riding for a few years. About a year ago my daughter and her husband (early 20s) got road bikes and ride with us once a week - usually around the 20-25 mile mark.
They felt that they were ready for something longer, so this past weekend we took a 56 mile ride (out and back) on a MUP, with a nice lunch break in the middle. Let's just say the OLD folks were doing MUCH better than the young whippersnappers at the end of the ride.
They are finally talking to us again!!