Ticket to Ride

It's early morning in August and the San Francisco weather forecast promises a warm and clear day. I'm walking through the house, stepping softly in my cycling cleats and trying not to wake my downstairs neighbors. I'm dressed in my cycling gear: black Lycra shorts with pink padding, white jersey and bright yellow windbreaker (in case the wind kicks up). On this day, I'm cycling solo. No buddies to check in with, no groups to keep up with and no men to impress.

My interest in cycling started when I became single after 15 years of marriage. It was my way of becoming physically and emotionally fit. I'm terrified of first dates; the anticipation sends me into a frenzied state. So I decided to replace the awkward evening dinner for cycling dates. You can cover so much more ground that way. There's no hiding, pretending or lying when you're cycling with a man trailing ahead or behind or nearby.

It's actually the perfect precursor to sex. I can instantly tell how skilled they are, what their bodies look like, how they move, the choices they make, how attentive, patient, fearful and cautious they are—just by judging their bike-handling skills. I can observe how their tight cycling gear fits; how they poured themselves like sausages into their bike jersey. I get to watch them glide, sweat, pant, climb and moan on their bike, and imagine how they'll perform in bed. A simple glance, a tired sigh, a wishful hug speaks volumes.

I've fallen in love and lust as much as I've fallen off bikes. I'll always remember the men I cycled with, even it was just a fleeting first date or a last ride before calling it quits. They each prepared me for the next one in my quest for finding love.

The Intrepid Dentist was my dentist for more than 10 years. We already had that intimate doctor/patient relationship, the kind where you trust them with your life or, in this case, my teeth. When he called me at home one night, to tell me his second wife left him for his best friend, I cautiously listened to his devastation from my couch. When he shared how he had been attracted to me for many years, and had fantasies of us, I fell for his bedside manner.

I was a cycling virgin before we rode together on the Sierra mountain trails through the Gold Country and Grass Valley. The ID raced bikes and knew how to handle them: he'd pick up my heavy bike with one hand and throw it over his right shoulder or load it into my car like it was a bag of groceries. But he didn't know how to handle the recent shock of his wife leaving him for his best friend and I wasn't prepared to deal with his emotional vulnerability. I wanted more than just to fix his broken wings.

The Architect had been introduced by a mutual friend and, by comparison, had great taste and understood beauty in all its various shapes and sizes. He brought his shiny new expensive Italian bike and I brought all the charm I could muster.

We cycled together along semi-rural Woodside Road, passing some of the billionaire homes in Silicon Valley. I lost track of where we were going because I was too absorbed in our flirty conversation. During our ride through the bucolic hills, while I followed behind him, I didn't notice the small black tacks that were neatly lined up alongside of the road, thwarting off cyclists.

"Uh oh! Wait a second, slow down," I yelled out out him. "I think my bike just ran over something."

"Don't tell me that. Are you serious?" he responded with an annoyed scowl.

As both my tires slowly deflated, I could see a dark cloud of disappointment tumble between us. Our ride was abruptly interrupted, as we walked my bike to a nearby gas station and luckily found another cyclist who offered to help.

We later went out for a drink and, while watching the beautiful sunset over Portola Valley, I wished we could press the refresh button and go for another ride sometime. But it was not to be.

Low drama and a big smile is what attracted me to The Marlboro Man, who was too cool to let his emotions stumble. When I met him one early Indian summer morning at an Arco station, I was filling up my gas tank.

"How's your morning going?" he asked and then tilted his head and noticed my bike in the hatchback of my car. "Where do you cycle?"

I enthusiastically responded and the next thing I knew, I had agreed to go riding with him in Marin. The most electrifying thing about TMM—other than his Irish good looks and surfer body—was that he was 10 years younger than me. At the time, I was in my late forties, and that carried a lot of weight on the confidence scale.

Unfortunately, he was married with a small child. And, suffice it to say, things didn't end well.

It took another year or so before I was strong enough to jump back into the dating pool. The Bro's OKCupid profile caught my attention. In his cycling gear, he looked sexy and confident on his mountain bike. We had instant chemistry and he grew to adore me—even the parts that would push him away when I was scared. He'd stay over on weekends and always brought his bike, as well as an unpredictable personality. Whenever he had an outburst, he'd storm out of my house. A few days later, I'd receive an icy text that asked, "When can I come by to pick up my bike?"

We pretended we could make our relationship work but we got ourselves stuck in an obsessive cycle of breaking up and making up. When we were cycling together one day, over the Golden Gate Bridge, he said, "The reason I'm in your life is to teach you about love." He was right. He taught me that love isn't always enough, no matter how much two people care about each other.

On today's ride, as I climb to the top of Mt. Tam and admire the San Francisco Bay landscape, I think about the various twists and turns of my cycling journey. My heart has been broken several times and badly bruised many more, and I've learned the way we arrive isn't always the same way we leave. I learned that I'm still pretty much a beginner.