It was March of 2007, another harsh New England winter was slowly winding down, and despite the fact that he already had literally dozens of friends on MySpace, Dennis was creating a Facebook account.
He had heard it was a cool way tolook at pictures of ex-girlfriendsreconnect with old friends. After creating his account and having his roommates proof read it, he decided to start searching for old friends from Minnechaug—which is not an Indian reservation, but rather where he went to high school.
He started with his graduating class of 1999, then the class of 2000, then the class of 2001, and then the class of 1967 to laugh at the hippies. As he began scrolling through the class of 2001, he came across the name “Jessica Brand, Boston MA,” and in an instant, a flood of memories came rushing in. These included memories of their time in school, in class—time spent together felt as if it had happened only yesterday, even though it had been eight years since Jess and Dennis had last seen each other.
Dennis sent Jess a message to say hello (again, following a quick copy edit from his roommate), and asked her what she’d been up for the last several years.
She ignored him.
So he tried again.
And again.
And again.
Finally, she relented and over the course of several email exchanges, they agreed to meet up at Salsa’s in South Boston, but only partly because they have the best guacamole in all of Southie. It was actually because both Dennis and Jess loved it and knew where it was. This was especially important for Dennis, as he often gets lost easily.
Jess had arrived early and was waiting for Dennis to arrive. As Dennis approached the restaurant, he could see Jess sitting at the table waiting and a sense of unease came over him because heforgot to put on deodorantrealized that it had been eight year since Jess has last seen him, and to put it nicely, he didn’t get better looking with age [Editor’s note: I agree].
Suddenly he became self-conscience, but remembered one of his favorite lines from one of his favorite TV shows, “Act as if ye have faith and faith shall be given to you. Put it another way, fake it till you make it.”
As he walked in, Jess looked over and smiled, and for the next four hours they talked, chatted and bantered as if they hadn’t missed a beat. The talked as if they were old friends getting reacquainted after some time apart, which kind of makes sense, because they were old friends getting reacquainted after some time apart. By the end of dinner, Dennis told Jess that they shouldn't wait another eight years before getting together again. Jess agreed and over the next couple weeks, they spend more and more time together.
Jess was leaving for a trip to Italy, so Dennis asked Jess over a pot of jasmine and vanilla tea if he could take her out to celebrate her birthday when she got back. By this time, Dennis was full on head over heels for Jess, but he wasn’t sure if she felt the same way. He knew he had to, as he would phrase it, “put on a full court press” to sweep her off her feet. She relented and agreed. She might have been drunk.
So for her birthday, he pulled out all the stops: romantic dinner in the North End, tickets to the Dave Mathew Tim Reynolds concert, and the use of a car service to drive them around town all night long.
Jess showed up at Dennis’ condo looking absolutely stunning. She rang the doorbell only to have Dennis’ cousin Mike answer the door with a giant samurai sword in hand. Before Jess could even ask why, Dennis was already out the door trying to keep his frustration and embarrassment from showing. Little did he then know that Jess didn’t mind the fact that Dennis and his cousin frequently act out scenes from the Teenage Mutant Ninja Turtles cartoon.
The night itself went absolutely to plan. The show was outstanding, the dinner incredible, the conversation engaging, and Dennis confident that he has lived up to his word.
Before Jess left for Italy he told her he wouldn’t make any promises about the night other than that it would be the best night of her life. [Editor’s note: Really Dennis? The best night of her life? Kind of setting the bar a little high there, don’t ya think? Next time, aim lower by suggesting it will be the best night of the week. That way, you at least have a one in seven chance of getting it right].
As the driver brought them back to his condo, Dennis told Jess that he still had to give her the birthday present he has gotten for her. She couldn’t believe that there was even more to what was turning out to be an amazing night.
When they got back to his place Dennis gave Jess her present. The gift was a framed photograph that someone had taken of the two of them at Dennis’ senior prom in high school. Dennis had told himself that if Jess cried at the gift that he would know for a fact that she felt the same way about him as he did about her. Jess looked at the picture, said it was really sweet, and gave him a nice friendly hug.
Just like that, Dennis’s spirit sank like the Titanic. His biggest fear had come true. He had fallen into the trap of the dreaded “friend zone” where no man wants to end up. Even worse, he had to blow through a good chunk of change on dinner, the car, and the tickets to get there.
Dennis decided right then and there that he wouldn’t say anything, that he would just keep his mouth shut [Editor’s note: It’s impossible for Dennis to keep his mouth shut].
The night was slowly coming to an end and Dennis was walking Jess out to her car. When they got to her car, Jess began playing with her keys attempting to delay her departure waiting to see if there was more to this night. Within those few seconds, Dennis had a change of heart and decided that he was going to take a shot and tell Jess how he felt about her and hope that she felt the same way.
Needless to say, she did, and here we are over four years later on the verge of watching these two kids tie the knot and continue their lives together as husband and wife.
Dennis has said many times that was the night that Jess swept him off his feet. They still haven’t touched the ground and, God willing, they never will.Thank you to Jamison Cush for editing our story.