Cleo’s Top 7 Valentine’s Dates (Ranked, Dah-ling)

One could say that I, Cleo, know a thing or two about love. And they’d certainly be right.

Julius Caesar crossed seas for my company. Mark Antony lost his head and quite a bit of Rome over dinner plans that went exceptionally well. Never underestimate the power of an exquisite Falernian wine.

When you, too, set your keen eye upon a lover, heed my advice. I have tested a thousand dates since 51 BC. What follows is my ranking of modern Valentine plans, arranged from impressively competent to absolutely divine.

7. Live Jazz Set

I was always fond of evenings shaped by a lovely lull of lyre. Such a refined instrument has fallen somewhat out of fashion, but alas, a dimly lit jazz bar will suffice nicely for your romantic evening.

Reserve a corner booth, close enough to feel the vibrations of the saxophone, lingering in the air like the trace of your lover’s perfume after a greeting kiss.

Oh, if only I could relive the evenings of sacred music and ritual dance along the Nile, sistrums chiming, drums calling the body to sway, and oil lamps flickering just enough to soften dear Caesar’s handsome profile. Judging by the low light and music loosening your posture at the jazz club, I can see that not much has changed.

6. A Fine Dinner

I always did adore it when my darling Caesar swept me off my throne and into a fine dining establishment. In my day, such places came with inconveniences, like smoky dining rooms and sand where it had no business being…so much sand.

You modern folk, however, have fine dining nicely under control. The floors are polished. You understand the power of a proper amuse-bouche. You respect a restrained dégustation. It’s honorable, if I do say so myself.

Before you leave the house, my little lovebirds, be sure to dress appropriately. I don’t want to see either of you in short-shorts or bucket hats – save that fashion for Coachella.

This lovely night is your chance to let your clothes do a little talking, perhaps revealing just enough to let the imagination wander. A concept you already understand, if you’ve spent any time with the gamble feature in A Night With Cleo.

5. Wine Bar Hopping

I see you’ve noticed the wine. Splendid. I suggested it earlier for a reason. Map out the finest wine bars within your region, and glide through the nighttime streets, sampling sip after sip of beige and burgundy heaven.

In my day, the art of tasting relied on careful progression. We began with Mareotic – or, forgive me, your modern world would call for a crisp Chablis. Your terrain could never quite replicate such a delicately perfumed white, born of the rich lakeside soils near Alexandria.

Move on to a structured Barolo or bold Cabernet as conversation loosens. And above all, serve absolutely nothing without a strong opinion as an accompaniment. For as I like to say, a bold assertion is the finest varietal of life.

4. Planetarium

You may recall that I’ve always had a fondness for the sky. Long before velvet seats and climate control, we read the heavens from temple ceilings, priests charting stars with solemn devotion.

Today, you have domes, lasers, and narration delivered tightly on schedule. It’s not quite as romantic as interpreting the stars by torchlight while frankincense burns low, but I suppose air-conditioning and surround sound shall suffice in a pinch. 

Settle into the dark and allow the universe to unfold above you. It’s difficult to feel rushed when you’re staring at something that predates your calendar by several millennia, much like your favorite Roman senator’s speech.

What’s that? You don’t yet have one? How unfortunate. In that case, you may substitute Gus’ latest bid for president. I’m told it’s rather riveting…if you’re into proclamations emerging from a man in suspenders.

3. Tour of Museums

Some romances benefit from a touch of movement.

In my time, this meant strolling through halls of sculpture, scrolls, and relics acquired by men who insisted they were conquerors. A-ha-ha. Excuse me for my indulgent chuckle, but conquest is so often a matter of perspective, and I think I would know.

Today, you have a grand choice of institutions, each far less pillaged and far better lit. When there, move slowly. Linger where you both find interest. Let one of you play the guide, even if the facts are slightly embellished, a habit I admit I share. Take it from me – confidence carries more weight than accuracy.

2. Solo Spa Day

I have always maintained that bathing is an art best practiced alone. In my time, this meant hours reserved for oils warmed just so, water infused with lotus and myrrh, and attendants dismissed. It’s a ritual fit for a queen, fittingly.

Valentine’s Day, contrary to popular belief, belongs just as much to the unattached. I assure you, despite what poets and philosophers might suggest, I never waited for company to feel adored, and neither should you. It simply isn’t noble.

So I hereby order you to book the spa. Take the full circuit, lingering in the steam rooms and soaking in the warm pools, feeling your shoulders soften until time loses its sharp edges. Perhaps you might spin a mythology slot between soaks.

1. Sunset Boat Ride

Romance is sweeter if it unfolds slowly with a breeze.

A private barge on the Nile, with silk cushions and musicians within arm’s reach, may no longer be accessible to you in this era, my eager lovers, but perhaps a boat ride before a golden sunset is.

Take your darling by the hand and help them carefully into a small wooden sailboat. Words matter very little on a date like this. Instead, give your attention to the gentle rhythm of the water and the molten glow of the sun slipping low.

When the moment feels right, lean in close and murmur something flattering enough to unsettle their judgment – an old favorite of mine. Or perhaps…simply smile.

Valentine’s Day, as you’ve now observed, is a test of discernment. Whether you dine well, drift beneath the stars, or indulge entirely on your own, enjoy the day with love on your mind.