The Longest Date

My valentine, my Frankenstein. Love's holiday rears up like a monster in my mind.

I'm old enough, wise enough, and sophisticated enough to know that Valentine's Day shouldn't matter. But it does. It really does. February 14 is a benchmark in life's journey, an “x” on the calendar reminding you that you're either in love or you're not. This year, I anticipate that Valentine's Day will dawn like any other. I am determined to shoulder through with no expectations — except if I'm surprised. Okay, I suppose that's an expectation.

Cynics claim that Valentine's Day has become a Hallmark holiday, a boomlet for the restaurant business, a night when no party larger than two can get a dinner reservation. Valentine's Day is not about red hearts, they say, but all about greenbacks.

I'm an optimistic romantic. No matter how many times I've loved and lost, I still think of Valentine's Day as Cupid's crucible. Even before February rolls around, I'm thinking of my valentine, either real or imagined.

“Valentine's Day sucks if you're single,” says Peter, my physical trainer, as I lay on the floor one day with my left leg in the air. Peter and I often find ourselves in what look like compromising positions, but I think of him as my kid brother. He's in his late twenties and looks like a blond surfer, though he comes from landlocked Vermont. Like me, he has yet to find true love.

I'm his client, but over the months that I've been working out with Peter, we've become friends. We discuss more than bicep curls and body fat. He gives me an unvarnished male perspective.

“I just started seeing this woman, and I'm not sure what I think about her. Already, I'm worrying about Valentine's Day,” he says. “What will she expect? If I'm still seeing her, I'll be polite and take her out. But I'm not crazy about her, so it just seems weird. Maybe I'll break up with her before Valentine's Day. That would solve the problem.”

“So Valentine's Day sucks more if you're dating someone who doesn't knock your socks off than it would if you were alone?” I ask him.

“Yeah,” he says, mournfully. “It's better to stay home with Chinese takeout.” Undeniably, men bear the burden of orchestrating Valentine's Day.

As Peter directs me to do 30 jumping jacks, I flash on my date last Valentine's Day from this new perspective. You might say that my past experiences propel me not only to stretch the hamstrings but also to tone the heartstrings. Last year, when I was seeing a man I thought I liked, Valentine's Day turned into a Throw Momma from the Train-wreck. I had so many illusions. I pictured a date so special that my heart would turn into raspberry Jell-O. I was ensnared in the trap of fantasy on a day that arrives wrapped in the red goo of expectations.

I should have known it would be a disappointment when my date waited until the morning of February 14 to ask me out. He called me on his way to work with this limp invitation: “We probably should go out for dinner tonight.”

“Yeah, that's a good idea,” I replied.

“Why don't you pick out a place you'd like to go,” he said. “I'll call you later.”

He hadn't planned anything special. He hadn't even made a reservation.

I admit I worked myself into a lather deciding where we would dine in intimate splendor. On a night when every high-end restaurant is booked, I thought of one swank downtown bistro where I knew the owner and could probably wrangle a table for two. When my date called later, I excitedly informed him of my choice. “Calm down, calm down,” he said. “I already have a place in mind.” He said he'd pick me up at 7.

I primped. I bathed. I balmed. I tried on and tossed a hundred outfits before deciding on a colorful quilted jacket with a short black skirt — sexy enough to send him seductive messages.

I had told him I would meet him outside so he wouldn't have to find a parking space. I'm too accommodating. I probably should have made him work harder. In hindsight, I should have lied and told him I already had a dinner invitation.

He called me on his cell phone from a block away, and I was waiting outside in the cold when he pulled up. He looked me over. “You're overdressed for where we're going,” he commented curtly.

“Geez, should I go back and change? I wanted to look nice,” I replied with an annoyed snap in my voice.

He condescendingly assured me I was dressed okay, as long as I didn't mind looking fancy at an unfancy place. He was taking me to the New Bridge Café in Chelsea. It's a steak-tip joint — jeans and sweatshirts, fluorescent lights, kids screaming at the next table. Surely, he'd fit in there. He was redolent of stale office, clad in undistinguished casual-Friday clothes (khakis and no tie). And it wasn't even Friday.

We rode across the Tobin Bridge in silence. Eros, the god of love, was not shooting arrows at us. The winged cherub was holding a gun to our heads.

I like the New Bridge Café and its funky charm. But not on Valentine's Day. The atmosphere doesn't hum with silky suggestion; it doesn't put you in the mood to do anything but pig out. There are no candles, no flowers on the tables — only checkered tablecloths and hearty platters of meat. I ordered the lamb, with a side of New Bridge's notorious garlic sauce. What was I thinking? Certainly not about breathing on anybody.

My Valentine's Day had turned into a Pyrrhic victory. Sure, I had a date, but at what cost? Quite cheap, given the prices at the New Bridge Café.

When we finally sat down, he handed me a card. I burst into giggles. “Calm down, calm down,” he said, in his cautionary Valentine's mantra. “It's nothing, really.”

“Oh, I love cards,” I said as I ripped into it, imagining for a split second that he had sent the very best. In fact, it was one of those cute but noncommittal cards with an unsentimental message I had trouble understanding at first (something about Shakespeare getting his start writing the slogans on candy hearts). He signed it with his name. No “love,” no “best,” not even a “regards.” I gave him a heart-shaped tin of Altoids. Then we redirected our passion to consuming the mounds of meat before us.

He didn't care enough to send the very best, and neither did I. If I had really wanted to be with him, pizza in front of the fireplace with Norah Jones for a soundtrack would have been enough. Valentine's Day is all about small, significant moments, not empty gestures.

My friend Mariamma describes herself as “on the shelf.” Having survived the dating wars, she says she's made her peace with being single. And yet she has a remarkable take on romantic matters. If Peter is my body coach, Mariamma is my soul coach. For years, she's been sharing with me her wisdom, which has helped me through many a malaise.

One wintry night over dinner in Harvard Square, I ask her how she reckons with Valentine's Day. I discover that Mariamma is touched by the fiery Valentine's spirit. “For folks who are together, it's a lovely excuse to show each other they care. I think that's wonderful,” she says. “I'm not reminded that I'm alone on Valentine's Day. I'm reminded that I once was a believer. For me, it's kind of like Santa Claus. Even if you don't believe anymore, you can still feel the innocence and joy. You can still remember the thrill of when you stayed up all night and thought you heard reindeer on the roof. It's the same with Valentine's Day.”

Mariamma vividly recalls when Sam, a man she dated in her early twenties, gave her an African doll and a mushy card for Valentine's Day. Her eyes get misty with the memory. Sam is long out of her life, but he left a mark. “Valentine's Day is about love in your life,” she says, “however you choose to think of it.”

Most singles would prefer not to think about it at all — at least not on the day itself — as they watch the roses pile up at the reception desk. For them, Valentine's Day is a run away from the roses.

As for me, I know I will have experienced a truly magical Valentine's Day when I wake up next to someone I love on February 15 and remember I forgot something. “Wow, honey, imagine that,” I'll say. “Yesterday was Valentine's Day, and it completely slipped our minds.”

Seems like the best way to celebrate love's holiday is to treat it like it's just another day.