John Curley met her on a train. His neck was sore from craning his neck to chat with her on the ride between New York and Philadelphia. He didn’t have her phone number or even her last name, but when they parted ways at the train station, he knew he wanted to see her again.

When it comes to love, there are no guarantees. You can take a chance with great success, or you can fall flat on your face. John Curley has experienced both the highs and lows when it comes to chasing after the girl of his dreams.

Her name was Stephanie. She lived in New York City, but was taking the train to visit her parents in Philadelphia. She went to Shipley School. That was it.

John knew someone that knew someone that knew someone that also went to high school at Shipley – so he asked for help. He wanted to get into the Shipley library to look at some old year books and find out Stephanie’s last name.

They told him he didn’t have to go to the school to find the yearbooks. So he trekked to Ludington Library in Bryn Mawr and sat down with a pile of the school annuals, and by the fourth one – he had found her. He opened up the phone book and found her last name – seven times, with seven different phone numbers.

He dialed one telephone number after another. ‘Do you have a daughter named Stephanie?’ he would ask each of the answerers. By phone call number seven, he had found her parents.

“Do you have daughter named Stephanie?”

“Yes, why?”

“Well. This is going to seem a little strange, but my name is John Curley and I met your daughter on the train coming back from New York. I know that she’s come to visit you …” and he gave her parents his phone number. He asked if it would be okay for him to call again, and if so, asked when would be the best time to get in touch with her.

“Why don’t we talk to her. You can call back at 5 and she may or may not answer.”

He did, she picked up the phone.

“I’m the guy on the train that was in the striped shirt that was talking to you.”

A second passed. She gasped; a gasp that could have meant “ew” or “how sweet.”

It meant “how sweet.”

It was a great start to beautiful relationship.

But chasing after girls didn’t always work out so well for John.

In college, he spent a summer in Ithaca, New York. He frequented The Moose Restaurant. It had terrible food – but that’s not why he was there. There was a waitress and she was gorgeous.

He showed up time after time hoping to get a seat in her section waiting to make his move. And he came up with the perfect plan. He rented a boat, made up a picnic, and went to the restaurant to ask her out.

She agreed, but disaster ensued.

They got out to the middle of Lake Cayuga and the wind died down. The two of them couldn’t sail anywhere, and the dream date John had planned turned into the date no one could escape from.

“Can we go back?” she asked.

John would have blown into the sails if he thought it would make the boat move and end the awkward trainwreck. Instead, he ended up battling with a warped oar banging his thumb against the side of the boat with every stroke to get them closer to shore.

“Could you do me favor?” the waitress asked as John paddled on. “If you’ve written me into one of your weird stories, would you mind writing me out?”

It was a long ride.

Sometimes that big, bold move just doesn’t end as well. And while things with Stephanie ended up great, it too wasn’t meant to be. After six months, the pair broke up.

Not before she gave John her grandfather’s watch: A watch that he loved and had no intention of giving back to her in break up penance.

But shortly after the relationship went bust, there was a knock at his door. Stephanie wanted the watch back. Sometimes after you take those big romantic risks – you’ve got nothing to show for it but a broken heart.