Not my first ride, but my wife's.
Years ago, friends and I started on hybrids. We busted our arses to do a 12 mile stretch, taking turns at the front, we made the stretch in 50 minutes. We were so proud.
We ended up improving some but I got a bike for my wife as well about a year later.
Rode around the hood, local streets, around the block, type rides just to get her used to the bike.
Took her down to the trail for her first trail ride. She ended up doing the 12 mile stretch in 45 minutes. Her first and she topped 6 months worth of the rides I had done with my buds.
Later we graduated to riding road bikes. We did a ton of forum rides various forums and sites. Even a few riders from other states visiting.
She ended up dropping 90% of the riders we met.
I knew from her first ride, she was a natural.