When Bad Dates Turn Great


It's not about the date, it's about the connection. Don't sweat the awkward first date.

Have you ever gotten your hopes up about a first date? Maybe this time? You almost can’t help having expectations. And the higher those expectations, the more likely you are to find yourself disappointed.

Sometimes those expectations are about the trappings of the date: are we going to the right restaurant, is the food good there, are we both looking good?

Not the stuff you need to care about. In the end, those things don’t matter in the slightest. Maybe they’re nice to have for atmosphere, but what really counts is the connection that you make or don’t make, regardless of what sort of date it is.

When Renee was a freshman in college, Aaron was a friend of some of her classmates. He asked her out, and she accepted. She assumed that he had plans in mind, but he didn’t. They ended up just going for a drive.

On the way back to her dorm he got pulled over for tailgating the car in front of them (according to the police officer). Aaron had to turn off the amp under his seat so it didn’t drain his battery, but that action made one of the officers suspicious, so he pulled Aaron out and searched the car. Renee was in the front passenger seat with Dunkin’ Donuts trash above her ankles – apparently it hadn’t occurred to him to clean out his car before a first date.

One of the cops shined a flashlight in Renee’s eyes while Aaron was being searched. The cop asked her if there was anything in the car that she should be aware of, and she said “I haven’t a clue; this is our first date.” The cop then asked her to kick around the trash by her feet, and she asked: “Do I have to? I’m afraid of what I might get stuck with.” The cop laughed and asked her if there was going to be a second date. She said it wasn’t looking good.

At the time, she had no plans of ever going out with him again because of the messy car, the lack of plans, and the fact that they got pulled over. I’ll let her tell the rest:

They let him go with a warning and when he got back in the car and pulled away he looked at me with this glimmer in his eyes and said "At least we have a good first date story for years to come." That look in his eye, and the fact that he was already thinking long term even though we hadn't done anything that night besides just talk, got him a second date. I still have to deal with trash on the passenger side floor of his car to this day, but every time I have to kick it aside I think of that first date and still get butterflies.

When Derek was dating his wife, he went one step further with the law. Elizabeth was subletting the apartment above him in Boston one summer, and they hit it off pretty quickly. They began dating, and she invited him to a semiformal dance at Wheaton College, where she was a student (he went to Boston University).

He’d been hanging out with his buddies, and they were all having a beer. But now Elizabeth was ready to go, and they all went to the car with their beers in their hands. As it happened, a police cruiser was rolling by at that moment, and saw his friend getting into the car with a beer in his hand. Derek watched and, while his friend was being handcuffed, he had discreetly hidden his own beer behind his foot. Just as he was about to leave, his beer tipped over, and he was busted, too.

The cop hauled the three of them in, and while they were spending a couple of hours in a holding cell, Elizabeth and their other roommate were busy arranging to bail them out. Eventually they were sprung, and Derek and Elizabeth hurried down to Wheaton. They arrived at the dance at 10 pm, an hour before it ended.

It would have been really easy for Elizabeth to be frustrated and furious with Derek for spoiling their evening, but she had a much healthier approach: she was amused by the entire thing, and rather proud that she’d bailed him out, and had a great time regaling her friends with the story.

She knew that Derek wasn’t trouble—this was his one and only run-in with the police—so she didn’t take the incident seriously. Instead, she took what could have been a disastrous date and made it into one of their favorite old stories.

These may seem like two lousy dates on paper, but they led to great things. You really can’t get much clearer than that: it’s not about the date, it’s about the connection.

Excerpted from the forthcoming book "The Last Place You Look".

Jim McCoy is a life coach, and one of his specialities is dating.  If you'd like help navigating your love life, contact Jim through his website at merlincoaching.com for a free consultation.