For years, I had been one to overthink what I should get for my valentine. What helped was that I had in years past been dating guys who found it refreshing that I like simple moments, like walking along a neighborhood street as dusk fast approached, hopping from shop to shop looking for a chocolate bar here, a coffee there, sit on a lakefront pier and pull each other closer in the chill, talking our heads off about nonsense.

What I liked, apparently, was something they wanted to experience, too, so that’s what they asked for on Valentine’s Day.

I’ve had nice Valentine’s dates that included the stereotypical fancy candlelit dinner at a Wicker Park restaurant, a chocolate and wine tasting in the Fulton Market District, coffee and cake at a corner cafe.

I’ve also had unconventional dates. Last year, before I returned from my vacation in Hawaii, I had pre-Valentine’s on a beach with a local boy over styrofoam takeout containers of Spam musubi and sodas, listening to the sounds of ocean waves crashing on the breakers while we made out on a park bench. A day later, I got a Valentine’s eve driving tour of Bellingham and Chuckanut in rainy Washington state.

A couple years ago, a guy I was with really didn’t believe that I actually enjoy those simple things I mentioned for such a special day like Valentine’s Day. He really pressed for a serious answer, “What do you really want, deep down?”

I’d argue that these are exactly what I want from a guy.

“But in your wildest dreams, what would you ask for?” he insisted.

I shrugged off the question because I didn’t really care. And I eventually shrugged him off, too, because quite frankly he wasn’t all that good at figuring out what I liked and didn’t like—in the general scheme of things.

But a recent conversation with a guy got me thinking about that question again.

You see, Samuel Hoehnle noted that the Bronx Zoo was offering a special Valentine’s gift opportunity this year. For $10 you can name a cockroach after a loved one—or not-so-loved one. For $35 you can also get a plush cockroach so your sweetheart can cuddle up to it each night. It’s quite the romantic reminder of how loved he or she is. Or not.

Maybe I’m geeky enough to like a gift like that.

I finally got to really thinking, if I could get anything in the world, what would make me feel special?

A most cheesy valentine

Cheeses and fruit

Have you considered naming a cheese for me for Valentine’s Day? Photo: Getty.

You cannot underestimate how fondue I am about cheese. I get excited when I walk into a shop like Pastoral Artisan Cheese, Bread and Wine in Andersonville. Without restraint, I may very well overturn every block and wheel. Imagine all de brie I might leave in the aftermath.

A gouda choice for a Valentine’s gift would be to make your way to a Wisconsin or European dairy farm to source your milk to take to a cheesemaker—to be cultured, coagulated, drained, scalded, aged or maybe ripened. I’d be impressed to be given a wheel of cheese made fresh, just for me, with me in mind from source to table. The idea is to me like Swiss—most hole-y.

Alternative:

Buy me some brie, fresh buffalo mozzarella, warm, hearty and rustic Italian or French loaves, fresh pears, figs, and plums, and a chilled bottle of Riesling. But the most important part is you joining me. I like the company. I like the conversation.

A pastry plan

Stan's Donuts for your valentine

How would you express what you know of me in an artisinal donut? Photo: Stan’s Donuts Chicago.

Matthew La Luz and I were driving around Chicago one night when we lamented that the city lacked a late night donut experience that wasn’t Dunkin’ Donuts. I like the hodgepodge found at places like Stan’s Donuts—a Hollywood, Calif. favorite that made it to Chicago. There’s also artisanal assortments at the Doughnut VaultFirecakes, and Glazed and Infused. But they just aren’t open on a late night when I most crave a fresh donut.

I admit I’d be dazzled by the thought of being led to a late night diner (if you can’t pay off the donut shop owner to let us in close to midnight) to be greeted by carafes of coffee and plates of several donuts from one of the these kitchens—a fully baked collaboration with one of their creative artisans.

If you could express what you think of me in a donut, how would it taste? How would you present island boy meets Midwestern metropolis, bookish but adventurous, whiskey bourbon bon vivant meets malted milkshake maven?

I find the romance in the thought put into crafting those donuts.

Alternative:

Make me several nut butter and jelly sammiches with fancy breads, creams and curds, jams and jellies of your choosing. A malted milkshake from a frozen custard shop might round out a moment sitting together, side-by-side, smiles with every lick and smack of all that ooey goodness.

Win me with whiskey

Whiskey in a glass

Be my valentine with a glass of whiskey. Photo: Getty.

There is always at least one bottle of whiskey available in my home. They’re standard fare—what I call “table whiskeys.” Jameson’s. Iwai. Suntory. Rebel Yell.

Now, I have to be careful in recommending this Valentine’s gift, knowing I might be prone to overindulging when I’m with someone I’m actually enjoying. It’s a double header of comforts: a swig and a sweetheart.

I enjoy the idea of being taken to a darkened room, table candles casting shadows dancing with each flicker of the flame. On the table are several bottles of whiskeys, an assortment of tipples ready to be carefully poured into Scotch and rocks glasses. A bucket of ice and short carafe of cold mineral water can heighten the peppery vibrancy of more youthful whiskeys. As for the dry dignity of a richer variety, I prefer to enjoy those unadulterated.

Such an evening would be well-rounded with smoked salmon and capers over lavosh, caprese bruschetta, and a tiramisu.

The best way to learn more about the craft of whiskey distilling is to drink as many kinds as one can enjoy. And it’s something I’d like to keep doing.

Alternative:

One bottle of slightly chilled whiskey with a prime rib or Italian beef sandwich on a comfy sofa, binging on episodes of the latest drama trends on Netflix and Amazon Prime can make a wonderful night. But I must still insist on a tiramisu.

Other ideas

Hairy Truman Hemingway cat

Hairy Truman, a cat at Hemingway’s Key West home. Photo: Ernest Hemingway Home and Museum.

Here are some further wild notions that came to mind:

  • Let’s drive from Chicago to Key West so we can hold Hemmingway’s six-toed cats in our arms.
  • Design an Indonesian shadow puppet for me and have an artist produce a Javanese wayang kulit drama to be shown for our friends.
  • Film yourself or a band performing “Lady in Red” by Chris De Burgh but change the words to “Gerry in Red.” This sounds more romantic if it’s you playing it on the ukulele.
  • Have a burger joint create and name a burger after me. Hold the pineapple, please! It doesn’t make it Hawaiian. And please, let there be avocados.
  • Hire out a taco truck for a neighborhood parking lot to serve us all the tacos and cervezas we want. Must have carnitas!
  • Rent out a movie theater for a private showing of a Doctor Who marathon and invite all our friends to come dressed up.
  • Run through the Art Institute of Chicago hand in hand until we reach Edward Hopper’s “Nighthawks.” We stare at it and consider that we are not all lost in our own worlds and thoughts, disparate lives trapped in an enclosed space.

What else do you think I’d enjoy? What would you enjoy for yourself?

In the end

As nice as it would be to fulfill anything off this silly, self-indulgent list, I find myself going back to simple pleasures. I’d need none of this. I’d be most happy spending an evening just walking a neighborhood street with someone.