We often ride in separate circles but sometimes ride together and do extended rides together. When we met 19 years ago she talked about having a good bike, a 250.00 nishiki mtb from the LBS and we did some small rides together. I kept encouraging her in her rides and made sure I didn't just constantly show her how much faster than her I was. This year we have plans to do the local mtb triple crown which is around 50 miles of non-stop mtb riding through 3 connected parks some of which can be fairly hard. We'll try the VTXL which is just over 300 miles and 3k feet of climbing which we hope to do in 4 days, either way we'll bail on day 4 since its all we can designate for the effort and we're hopeful to do the Super8 in VT as well. But most of her riding will be with friends or the kids while most of mine will be solo, with the kids, or trailing the oldest's cycling group as a sag assist. The oldest and I are planning century rides every couple weeks to get ready for some grand fondos this year.