One day, Colleen walked up to me, looking a bit confused, and said, “Your friend over there told me you had something to ask me.”
She pointed behind her, and I saw Jerry in the distance smiling and winking at me. I mentally cursed him.
“Uh, yeah,” I stammered.
She waited patiently, and I finally mustered the courage to go for it. “I was wondering if you’d like to do something together sometime.”
She looked thoughtful at first, and I braced myself for rejection. But then she smiled brightly and asked, “Are you asking me out?”
Her enthusiasm gave me the confidence to respond. “Yes, I am. Would you like to go out with me?”
She handed me a piece of paper with her number. “Call me tonight.”
Seeing my confusion, she laughed. “Your friend bet me you wouldn’t ask me out because you were too chicken.”
“Really?” I glared at Jerry.
“Yep, but I had faith in you. Now I’m ten dollars richer thanks to you.”
“Happy to help. Let me know anytime I can make him a loser,” I joked, and we both laughed.
She said goodbye and reminded me to call her after 8:00. As she left, Jerry walked over with a smug look.
“What’d she want?” he asked, pretending to be clueless.
“She came over to tell me what an intrusive a-hole you are,” I replied, throwing a towel at him.
He laughed and shrugged it off. That night, I faced another dilemma. I hadn’t been on a first date in over a decade. I had no idea where to take Colleen or what to expect.
Were the dating rules still the same as when I courted Paige? My mind raced with questions. Dinner? A movie? Something more adventurous?
Surprisingly, Lance gave the best advice.
“I always take a girl somewhere unexpected. Dinner and movies are boring first dates and can get you friend-zoned. Do something unique, like taking her to a weapon range or batting cage. Excitement works every time.”
I couldn’t think of anything I could teach her, but then Lance suggested, “Why not go for a bike ride? Didn’t you meet her in a biking class?”
I asked Colleen, and she was excited about the idea. So, that Saturday, we packed our bikes into my SUV and headed to the trail. But what seemed like a good plan quickly backfired. Biking on a first date turned out to be a sweaty and awkward way to get to know each other, leaving little room for conversation.
When we did take breaks, we were too busy catching our breath to talk much. I started to worry the date was a bust, and Paige’s taunt about me being boring echoed in my mind. Then something unexpected happened. A panicked kid ran up to us yelling incoherently.
We tried to calm him down, but he was too upset to make sense. Eventually, he waved us to follow him. When we got to the spot, we saw a man lying on the ground, desperately holding on to someone dangling over a cliff.