The Portland Phoenix

Leftovers: Heard it in a love song

Natalie Ladd

When the devastatingly handsome Landscaper paved over my heart the second time, my friends circled the wagons for an intervention. Tired of watching me not learn from my mistakes, they went tough love on me. At one bachelor friend’s urging, I became convinced my blinded lack of judgement warranted a professional dating service.

Embarrassed to part with money to get a date, my opinion changed after investigating a well-reputed operation. There were questionnaires, cynicism-dousing conversations, safety assurances, and an interview over wine and an appetizer so the matchmaker could see if I had social graces. The guy knew what he was doing.

As fate would have it and unbeknownst to me, the Landscaper joined the same service (ouch) and his profile was the first one sent to me by the service. While there were no names or pictures accompanying the extensive dossier, I absolutely knew it was him. Saying nay to the matchmaker who confirmed my suspicions, I asked he never share my information with the “uncannily perfect match” that came my way.

After venturing out on a few dates with “appropriate” men (yawn), I accepted the fact that I needed time alone, and most likely a new therapist. The investment I had made was ultimately for myself alone; I started wondering how many cats I should adopt.

Then, I heard about a must-see band playing at Lenny’s at Hawkes Plaza in Westbrook. Formerly of Empire Dine & Dance, legendary hospitality owner Bill Umbel had spun magic on this funky little place with the outstanding food, stiff drinks, and relaxed but efficient servers. Thinking I’d drag BFF, I bought two tickets (music is usually free) and made a reservation at my favorite high top.

Upon occasion, BFF’s family obligations get in the way of our Thelma-and-Louise-like behavior, and that evening proved to be one of them. Instead, I asked one of the men I had previously spoken to, but never met, if he’d like to accompany me to Lenny’s. I bought the tickets and he would buy dinner. In my mind, it was a friendly arrangement, with the emphasis on friendly.

Arriving early the night of the show, I had a chance to chat with the server, who was a kindred spirit in many ways. We stopped talking, but made knowing eye contact when my companion sat down. Nice enough, but Lenny’s was not his comfort zone and conversation was stilted.

Then, a guy walked in and joined us at our table, which was a mandatory four-top on this sold-out evening. Explaining his brother couldn’t make it, the three of us talked and I found myself thinking he was smart, interesting and undeniably hot. The attraction was mutual, but he was a gentleman and I wasn’t a mean girl.

Then, I got an idea.

My companion was obviously not enjoying the atmosphere, so after the first set, I asked if he’d had enough. He said he had, and I offered to walk out with him.

And then I told the server, “Buy that hot guy at the table a beer. I won’t be more than five minutes.” Waving goodbye to Bill, I walked out.

Parting was cordial and I’m sure my companion was relieved. He high-tailed a left out of the parking lot and I got in my car and took a right.

Then, I went back.

There were innocent sparks at the high top that night and while my tablemate and I had a blast, there was no real connection beyond the thrill of spontaneity and appreciating the music. I still bump into him around town now and then, and our friendly greetings always make me smile.

One thing did stick that night. I knew for sure I was going into the “You can’t make this stuff up” file at Lenny’s, giving staff something to laugh about at closing.

In this case, that special file is a cool place to be. And, I overtip that server at every opportunity.

Natalie Ladd is a Portland restaurant veteran, freelance writer and connoisseur of all things Bruce Springsteen. She loves Boston sports, chewy red wine and has never sampled a cheese she didn’t like. She can be reached at

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