When religious authorities in the late Roman Empire moved to suppress the pagan festival of Lupercalia and elevate a feast day honoring the Christian martyr Saint Valentine—who, to this day, remains something of a historical mystery—they had no idea how widespread, commercialized, and romance-obsessed the holiday would eventually become. And guess what, sir—you, the one reading this, get to foot the bill for that centuries-old decision and its cultural legacy.

If you’re in a relationship, you’d better deliver. Even if your lady insists she isn’t overly concerned with the “small stuff,” the truth is that—speaking as a former hopeless romantic and lifelong traditionalist when it comes to this aspect of dating (when I am dating, because I’m thoroughly enjoying the single life at the moment)—it’s still your job to court. And as long as you’re with someone, that’s a job you never really get to clock out of (said with equal parts sarcasm and sincerity).

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In this piece, I’m offering a list of romantic date ideas. I’m well aware that most of us aren’t operating with a Hollywood-sized budget, so these suggestions run the gamut. As someone who admittedly over-plans, I once created spreadsheets packed with date, vacation, holiday, and birthday ideas spanning years—ready to be deployed at a moment’s notice (yes, I am a certified nerd). I can say with confidence that in past relationships—even when things eventually soured—one area where I was never criticized was thoughtfulness. As a shorter guy, this one element of relationship etiquette has always helped me stand out.

Without further ado, here’s a list of Valentine’s Day date ideas for her.

DINNER  

RODIZIO-STYLE ALL-YOU-CAN-EAT STEAKHOUSES

These never get old. There are plenty of chains, and many of them manage to feel exclusive despite the all-you-can-eat format. In the New York metro area, the most popular options are Texas de Brazil and Fogo de Chão, with the latter being my personal favorite. Servers come to your table with various cuts of meat, while the rest of your plate is handled via a well-stocked buffet. I’d strongly recommend considering location—take a minute to Google interior photos. Once you land on a good one, the experience is almost always positive.  

"EXOITIC" OR LESS CONVENTIONAL RESTAURANTS

I’d skip the usual Italian, Chinese, or Spanish restaurants—not because they aren’t great, but because those cuisines are oversaturated and, in my opinion, better suited for other occasions. Instead, look toward Thai, Nepali, Turkish, Nigerian, hibachi-style, or fusion restaurants. In New York, Cabana is one fusion spot I swear by, blending Latin American influences with a lively atmosphere. Years later, one ex-girlfriend still reminded me of the Thai restaurant I once took her to—proof that thoughtful choices stick. Thai Villa on 19th Street in Midtown Manhattan is a great example: elegant, visually striking, and priced reasonably enough to justify the experience.

DAY TRIPS

Sticking with the idea of giving her an experience she’ll remember, here are a few short-trip ideas. You can easily combine these with the dinner options above to plan out a full day.

HELICOPTER RIDE

Here in NYC, Blade has been heavily advertising helicopter rides in the $175–$225 range, primarily for commuters traveling between Manhattan, JFK, and Newark. If you’re near any major metropolitan area, chances are there’s a similar service available. While commuter-based, if you’ve never been in a helicopter, it makes for a memorable experience. Not interested in riding together? Get her a ticket so she can take a helicopter home from work one day instead of sitting in traffic.

WEEKEND COTTAGE GETAWAY

One year, I took a girlfriend to the Poconos for the weekend. The cottage included a Jacuzzi at a very competitive price, and the surrounding area offered everything from zip-lining to shooting ranges. It made for an unforgettable weekend. Consider something similar in your area—the Catskills if you’re in New York, or mountain and lake regions elsewhere. Most people don’t realize how many options are within a few hours’ drive.

SPA VISIT

Probably not the most unique gift, but what woman—aside from the most obsessive-compulsive germaphobe—doesn’t appreciate a self-care day? As always, read reviews and look at interior photos. Many spas offer package deals that include massages, pool access, and gift cards that allow flexibility. You can make it more appealing by turning part of it into a date, while also giving her a gift card she can use solo later on (maybe on a day when she’s particularly stressed out—with you).

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THE ARTS

Romance is the theme here, so I’ll spare you suggestions involving sold-out arena shows geared toward metal, hip-hop, or EDM fans. For couples, intimacy is the point.  

SMALL JAZZ CLUBS

Musical tastes vary, but it’s hard to beat a hole-in-the-wall jazz club for an intimate live-music experience. Even if you’re not a jazz person, there’s something undeniably exciting about watching a small group perform just feet away. In New York City, places like Birdland, Smalls, and the Village Vanguard come to mind. Most have a one-drink minimum and solid finger food.  

OFF-BRODWAY AND SMALL THEATER

Even smaller cities tend to have at least one local performance venue worth checking out. Off-Broadway productions—often staged in tiny theaters—create a more intimate experience. You can whisper, lean in, and actually focus on the dialogue. Smaller productions tend to rely more heavily on storytelling than spectacle, which makes the experience feel more personal. Plus, most of us have already seen The Lion King, Wicked, or Blue Man Group at least once.

Paint-and-sip nights have their place—great for early dates or random nights out. But for couples who’ve been together longer and want something more memorable, these ideas hit harder.  

COFFEE CLASSES

New York–based 787 Coffee offers a “Learn Coffee in Puerto Rico” experience that takes you directly to their coffee farms. You’ll learn about growing, processing, roasting, and brewing over a two-day intensive. Prices start around $1,200. If that’s a bit much, private brewing classes at their New York locations run closer to $250. Why include this? Because the focus here is on unique experiences—and this definitely qualifies.

WINE CLASSES AND TASTINGS

February isn’t the ideal time for vineyard activities in the Northeast, but wine experiences don’t disappear in winter. Regions like the Seneca Lake Wine Trail offer seasonal events such as wine-and-chocolate pairings, which fit Valentine’s Day perfectly. Closer to the city, spots like Macari Vineyards on the North Fork or Millbrook Winery in the Hudson Valley offer tastings year-round. Save harvest-season activities for late summer or early fall—but don’t rule out winter wine weekends entirely.

THE SMALLER THINGS

While most of this piece focuses on bigger gestures, the smaller ones often carry more emotional weight.  

   
1. eCards – A thoughtful message first thing in the morning goes a long way.
   
2. A Real Greeting Card – Taking the time to write something by hand still matters.
   
3. Printed or Polaroid Photos – Physical memories last longer than scrolling.
   
4. Flowers – Timeless for a reason.
   
5. Chocolate – Godiva bags, assortments, or an absurdly large bar all work.
   
6. Cake – Buy the whole cake, not a slice. Remember her favorite.
   
7. Rose Petals – Classic. Cleanup is annoying, but the reaction usually makes up for it.

I distinctly remember an ex-girlfriend of mine posting a photo of her with a caption celebrating our relationship with her holding the five-pound chocolate bar I bought for her to boast about its size. It was something she brought up regularly in conversation when telling the many reasons why she was so into me. The little things will often create the biggest memories. 

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CONCLUSION

Valentine’s Day is a commercial mess—we all know this—but that doesn’t get you off the hook. You should be showing love year-round; Valentine’s Day just forces you to do it in overdrive. Don’t treat February 14th as a way to make up for neglect during the other 364 days. She’ll notice that more than anything you do on the fourteenth.

We hope this list gives you some solid ideas—and maybe even makes Cupid a little jealous. What’s the most romantic thing you’ve done on Valentine’s Day? Share your experience and join the conversation on our forum. Cheers.

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