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Valentine’s Day is one of the most stressful holidays of the year for a lot of people.
I’ve watched friends spiral at the thought of planning the perfect date, picking the right gift or coming up with something original once mid-February rolls around. And honestly? I get it. Even the most romantic among us can hit a creative wall when we’re trying to plan something meaningful — especially when expectations are high and chocolates are overpriced.
So here’s a suggestion that might actually take the pressure off: use an AI chatbot.
Bookmark this post and come back to it every February — you’ll thank me later.
1. Arrange amazing plans for your V-Day date-night
Putting something lovely together for the actual evening when you and your partner head out for a lovey-dovey handout is tough. Before you make those expensive reservations at a five-star restaurant or any other place of your choosing, it might be best to revert to Gemini for some assistance. A prompt like this will work:
“Plan a 3-stop Valentine’s Day date in [City Name] that includes a couples massage, a restaurant with skyline views, and a dessert spot.”
It could also be worth asking the AI for ideas on how to set up dates based on different concepts, such as picking the best places in your hometown for roller or ice skating, pottery or cooking classes, and art galleries or live jazz performances.
Luckily, Gemini helps find available reservations for your favorite restaurants. It will even go as far as bringing up booking platforms and putting a list of all the options you can reserve.
2. Find the perfect wines to pair with your entree for the evening
So you want to get extra fancy with your partner during a night in for some home-cooked dinner. The perfect drink to accompany your choice of entree should be some sort of wine, correct? This loaded prompt is just an example of what you could ask Gemini as your wine expert:
“I'm making spaghetti with chicken parmigiana and a side of roasted brussels sprouts for Valentine's Day. Recommend three distinct wine pairings: one classic, one adventurous, and a cheap option under $20. Explain why each wine complements the meal."
I used these prompts and it gave me these three delectable choices:
- Chianti Classico (Sangiovese): Chianti (especially a Classico) is the quintessential Italian red for tomato-based dishes. Its bright acidity matches the tang of your marinara sauce and cuts through the richness of the cheese and breaded chicken. Earthy herbs and savory notes also play nicely with roasted Brussels sprouts
- Orange Wine (Skin-Contact White): Orange wines (white wines made with skin contact) have texture and tannin that give them almost red-wine energy, yet they’re still aromatic like a white. They’ll pair beautifully with both the tomato sauce and the roasted Brussels sprouts’ nuttiness. Think of it as a fresh, funky bridge between your components
- Montepulciano d’Abruzzo (Under $20): Montepulciano delivers great value with juicy berry fruit and balanced acidity that plays well with tomato sauce and rich, cheesy chicken. It’s usually medium-bodied and forgiving — hearty enough to stand up to this meal without overshadowing it
Feel free to pick up a bottle of any of those three picks if you’d like.
3. Come up with creative and thoughtful gifts
You can go the simple gift-giving route if your partner is easy to please. Or you can go deeper and find something that perfectly complements their favorite celebrity, book, clothing brand, or whatever else they’re super into.
Now you could ask your Gemini-turned-V-Day planner, “show me heart-themed items under $50 that look high-end," or get more specific and ask, “my partner loves books written by Nicholas Sparks. Show me his most recent books, where I can buy them, and their lowest prices.”
Getting creative (or basic) as possible with your V-Day gift giving becomes an easier process with AI, giving you plenty of options to choose from.
4. Plan a getaway together
If you and your partner have ever taken a trip you still talk about — maybe a sun-soaked getaway, a romantic city break, or a food-focused adventure — Valentine’s Day is a great moment to bring it back into the conversation.
Instead of trying to guess the “perfect” next destination on your own, let Gemini do some of the brainstorming for you. Try a prompt like this:
“My partner and I loved our trip to [Location] last year. What are a few destinations with a similar vibe that we could consider visiting in 2026? I want to bring one up during our Valentine’s Day date.”
This gives you thoughtful, tailored options you can casually work into conversation — without the stress of planning an entire trip on the spot.
5. Add some great rom-coms to your streaming playlist for a chill evening
If you and your partner would rather stay in for Valentine’s Day (honestly, same — especially if you’re dealing with brutal winter weather), a low-stress plan is to curl up with a great rom-com.
The problem? There are so many options that picking just one can turn into its own mini date night debate. To spend less time scrolling and more time actually watching, let Gemini narrow things down for you with prompts like these:
- “What are some rom-coms currently streaming on [Streaming Service] that use the friends-to-lovers trope and were released in the last 10 years?”
- “What are some rom-coms currently streaming on [Streaming Service] that use the enemies-to-lovers trope and were released in the last 10 years?”
- “What are some rom-coms currently streaming on [Streaming Service] that use the accidental-lovers trope and were released in the last 10 years?”
These prompts help you zero in on exactly the kind of romance you’re in the mood for — without the endless browsing.
6. Get the kids involved
So you’ve already locked in your Valentine’s Day plans. If you have young kids, you’ve probably arranged for them to spend the evening at a grandparent’s house or with a babysitter while you’re out.
Before you head out the door, you might want to make sure your little ones have their own plan for a fun night — not just a long stretch of screen time.
Here’s a simple prompt you can give to Gemini to help set them up with activities they’ll actually enjoy:
“My [age] child/children will be staying at my grandparents’ house while we’re out for Valentine’s Day. Their favorite things are board games, coloring books, and toy cars. With those interests in mind, what are some fun activities you’d recommend for them?”
7. Plan a memorable Galentine's Day for you and your closest gals
Here’s a special bonus AI search tip for any ladies out there who are basking in the joy of Galentine’s Day instead of Valentine’s Day. For those of you not in the know, Galentine’s Day is celebrated on February 13 and is a global holiday that’s all about celebrating women’s friendship. If you’re an avid Parks and Recreation fan, then you already know how this holiday first came into existence.
Work with this AI prompt to set you and your girlfriends up with the perfect hangout the day/night before all the couples take over everything for Valentine’s Day:
“My group of [Number] girlfriends and I want to celebrate Galentine’s Day. We live in [City Name] and want to go to a nice Italian restaurant and a karaoke bar afterward. Give me some recommendations for both.”
Bottom line
Setting up a memorable Valentine’s Day celebration shouldn’t stress you out—it should be a relaxing affair, especially since Gemini can step in to give you some valid recommendations for whatever you’re planning.
Put these tips to good use and refer to them every year before every V-Day to make your annual planning period less of a chore. Fingers crossed that your plans impressed your partner and got you extra kudos for the biggest lovey-dovey holiday all year round.
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More from Tom’s Guide
- 27 Valentine’s Day gifts that look way more expensive than they are
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- Staying in with your partner on Valentine’s Day? These are the 9 best couch co-op and two-player games to play on a cozy night-in
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