Valentine's Day isn’t just for new couples or hopeful romantics—it’s for everyone, including those who have been together for years, even decades. Many people look for creative and romantic ways to spend Valentine's Day, making it a memorable occasion for their loved ones. 

Whether you’re crushing on someone, dating, engaged, or married, asking, “Will you be my Valentine?” is a sweet and meaningful gesture. It’s a chance to express affection, rekindle romance, or simply remind your partner how much they mean to you. The beauty of this tradition is that it can be as simple or elaborate as you want. 

No matter the stage of your relationship, taking the time to ask thoughtfully can bring joy to both of you. But when is the right time to ask? And how do you go about it in a natural and exciting way? Let’s dive in.

If you’re looking for spiral bound books for couples and relationships, check out our collection at Lay It Flat! We create spiral bound versions of the best couple books, allowing you to lay them flat while reading with your partner or significant other. Say goodbye to having to press your books down constantly, and grab a spiral bound book today!

Understanding Valentine’s Day

Valentine’s Day is celebrated on February 14th, a day dedicated to love and romance. Its origins trace back to ancient Romans celebrating matchmaking and fertility. Later on, Christian traditions related the day to Saint Valentine, a martyr who, according to legend, secretly married couples against Roman law. This special hearts day evolved over centuries into the holiday we know today. People around the world mark this day by showing appreciation for their loved ones, friends, and family members through gifts, flowers, and heartfelt messages.

In contemporary times, Valentine’s Day is a prime occasion for couples to go on romantic dates and enjoy grand romantic gestures. Whether it’s a candlelit dinner, a surprise getaway, or a simple yet meaningful gift, the day celebrates love. On the other hand, singles or non-partnered individuals also find creative ways to enjoy the day. From blind dates to fun activities with friends, everyone really finds a way to embrace romance. Whether in a relationship or enjoying the company of friends, love is definitely in the air on the 14th day of February.

When is the Right Time to Ask?

Timing is everything, but there’s no one-size-fits-all answer. Waiting too long to ask could make the person feel like they were a last resort, which you definitely want to avoid. Your approach will depend on your relationship status, comfort level, and personal preferences. Asking too early might seem premature while asking too late could feel like an afterthought. Being mindful of timing ensures that your Valentine’s Day plans are well-received and not stressful.

1. For New Crushes or Potential Valentine's Dates

Timing can make all the difference if you’re asking someone you’re not yet in a relationship with. Asking too soon—like weeks before February 14—might come off as overly eager, while asking on the day itself could make it seem like an afterthought, similar to planning a first date. Ideally, a week or two before Valentine’s Day gives enough time to plan a date but keeps the excitement fresh. Understanding the person's preferences can help you decide whether to go for a grand gesture or keep it simple and casual. Consider their personality as well—some people love spontaneity, while others prefer a little notice. A casual conversation about Valentine’s Day can help you gauge their interest before making your move. If you sense enthusiasm, go ahead and make your ask with confidence!

2. For Couples in a Relationship

If you’re already dating, there’s no pressure to wait for the perfect moment. Planning Valentine's dates can be a fun way to keep the excitement alive in your relationship. Even if it’s expected, asking in a fun or romantic way can make your partner feel special. Some couples use it as a playful tradition, even if they’ve been together for years. You might want to bring it up over a cozy dinner or leave a heartfelt note somewhere they’ll find it. The key is to keep it sincere and thoughtful—the little things matter most. Even if you’ve celebrated many Valentine’s Days together, continuing the tradition of officially asking can keep the romance alive.

3. For Married Couples

Just because you’re married doesn’t mean you should skip the fun of asking! Consider going old school with your approach, like writing a love letter or planning a surprise serenade. In fact, many long-term couples forget to make a big deal out of Valentine’s Day. A simple but heartfelt invitation to be your Valentine can bring back that spark and remind your spouse that they’re still the one. Surprising them with a sweet message or planning a romantic evening can make the day feel special again. Even if your partner knows you’ll celebrate together, officially asking keeps the romance alive and exciting. Consider making a tradition out of it by asking in a different creative way each year!

4. For Friends and Family

Valentine’s Day isn’t just about romantic love. Many people ask friends, parents, or children to be their Valentine as a sweet way of showing appreciation. You can also ask a friend for advice on making the day special for your loved ones. In these cases, any time leading up to February 14 works! A heartfelt message, a small gift, or even a fun card can brighten someone’s day. If you have kids, making Valentine’s cards together can be fun to celebrate the day with them. Including family and friends in the celebration of love can make the holiday more meaningful and joyful.

Preparing for the Ask

Before you pop the question, “Will you be my Valentine?” it’s essential to consider the other person’s preferences and feelings. Think about what makes them feel special and what kind of romantic gestures they appreciate. If you’re planning a grand romantic gesture, ensure it’s something they’ll enjoy and not feel uncomfortable with.

Timing is also crucial. Asking too early or too late can affect the response. A good rule of thumb is to ask a week or two before Valentine’s Day. This gives your Valentine enough time to think about it and plan accordingly. If you’re planning a fun day or a scavenger hunt, include activities that you and your Valentine will enjoy. You might even consider involving their friends and family to make the day even more special.

How Do You Actually Do It?

The way you ask depends on your personality and relationship. If you plan to ask a girl, consider personalized and heartfelt ways to make her feel special. Whether you’re direct, playful, or romantic, the goal is to make the other person feel appreciated. Here are some easy, heartfelt ways to do it:

1. The Classic Approach

A simple, direct, genuine "Will you be my Valentine?" works perfectly. Sometimes, less is more. Looking into their eyes and asking sincerely can make the moment feel intimate and meaningful. A handwritten card with a heartfelt message can also add a personal touch. If you’re nervous, a small gift like flowers or chocolates can help break the ice. This approach works well in any type of relationship, from new crushes to long-time partners.

2. The Playful Method

If your relationship is full of humor, make it a joke! Send a funny meme, write a silly poem, or create a fake contract asking for their Valentine’s Day commitment. Lighthearted gestures can make the moment fun and stress-free. This is especially great for couples who love to joke around and keep things lively. Playful teasing or a surprise message hidden in their daily routine can work wonders. If humor is a big part of your relationship, lean into it and make the ask memorable.

3. The Romantic Gesture

Flowers, chocolates, or a handwritten note go a long way. Even if you’re married, surprising your spouse with a thoughtful question in a card can make them feel extra loved. Consider planning a special date and making the ask part of the experience. A candlelit dinner, a heartfelt letter, or even a spontaneous dance can make the moment truly magical. The effort you put in speaks volumes about your feelings. Romantic gestures never go out of style; even the simplest ones can make a lasting impression.

4. The Digital Ask

For those in long-distance relationships, a heartfelt text, voice message, or even a video call can make the moment special. You could also email a cute e-card or a short love letter. A well-thought-out message can make your partner feel loved even from miles away. If you're tech-savvy, consider making a short video montage of your best moments together before popping the question. Distance doesn’t have to be a barrier when it comes to showing love and appreciation.

Best Books for Couples Celebrating Valentine’s

1. A Year of Us: A Couples Journal: One Question a Day to Spark Fun and Meaningful Conversations

Keep the fire burning with your husband or spouse with A Year of Us: A Couples Journal.

Deepening your bond with your partner with this modern couple's journal only takes a few minutes a day. Covering everything from the lighthearted to the heartfelt, this book will strengthen your connection as you explore engaging prompts over the course of a year.

What sets this daily journal apart:

• Daily questions: Enhance communication with 365 prompts that spark everyday conversation and provide enough space for both partners to respond.

• Variety of prompts: Broach all important aspects of your relationship with smartly curated prompts that address your goals and dreams, past and present experiences, sexual and romantic desires, and more.

• Guided growth: Opening and closing reflections offer an opportunity to chart how you change over the year and how your partnership evolves through journaling.

Kick-start a year of conversation and connection with this revealing couple’s journal.

2. Date Night Cookbook and Activities for Couples: Recipes and Games for a Romantic Night In

Rev up the romance without making a reservation!

Couples don't need extravagant experiences to foster a strong relationship―you can connect and have fun right in the comfort of your own home. Date Night Cookbook and Activities for Couples provides uncomplicated recipes designed for two, plus bonding activities that make date nights deliciously fun.

What sets this date-night-in cookbook apart from other couples cookbooks:

• Simple recipes and complete menus―Each date night menu includes a main course, one or two sides, plus a fun extra recipe, like a dessert. You also get tips on what to drink from your menu.

• Tips for two cooks―Work together in a well-choreographed culinary dance using advice for shopping, prepping your kitchen, and divvying up tasks between chef and sous chef.

• Games for getting closer―Keep the conversation flowing with activities and questions that come with each menu. You'll discover new things about each other, laugh together, and express your love creatively.

Focus on each other and "get away from it all" without having to go out using this engaging cookbook for couples.

3. 5-Ingredient Cooking for Two: 100 Recipes Portioned for Pairs

Cooking for two has never been easier―or more delicious!

With easy-to-follow instructions, smart shopping lists, and step-by-step meal planning, the 100+ recipes in 5-Ingredient Cooking for Two help minimize prep time while maximizing flavor and your budget. Each dish is perfectly portioned, from Breakfast Quesadillas to the fresh take on Weeknight Fish Tacos. And don’t miss the S’mores Cookie Cups!

This essential couple’s cookbook has more than just tasty and wholesome recipes inside. You’ll also find invaluable tips for streamlining your kitchen time, reducing food waste, and enhancing your meals with cooking hacks and simple techniques to add even more flavor to your favorite dishes.

As with the best cooking for two cookbooks, this one features:

• Perfect portions―Each recipe, whether a traditional entree, breakfast staple, or indulgent dessert, makes two generous servings and is crafted to make cooking for two easy.

• Time-saving tips―From one pan/pot meals to dishes you can make and freeze to kitchen shortcuts that reduce cleanup, this cookbook is a must-have for busy twosomes.

• Enhanced eating―Recipes include creative ways to upgrade your meals with imaginative garnishes, scrumptious variations, and pairing tips.

At last, an innovative 5-Ingredient cookbook is designed to deliver on taste for any twosome while respecting your time and budget. Dig in!

4. Love More, Fight Less: Communication Skills Every Couple Needs: A Relationship Workbook for Couples

Conflict is part of every relationship, even the healthiest ones. The key to a long-lasting relationship isn't avoiding fights but seeing them as opportunities to work together. In her book, Gottman-certified relationship coach Dr. Gina Senarighi gives us the tools and strategies to communicate effectively, rebuild trust, and repair past hurts.

Love More, Fight Less features:

• 30 COMMUNICATION SKILLS AND ACTIVITIES for building self-awareness, identifying and interrupting emotional reactivity, eliminating judgment, separating thoughts from feelings, and more

• 29 COMMON PITFALLS IN RELATIONSHIPS around issues of intimacy, career, finances, family and home matters, and friendships with other people--and how to navigate them

• STEP-BY-STEP GUIDANCE AND EXPERT INSIGHT to help you transform your relationship's conflict patterns by integrating effective communication skills

This relationship workbook is for couples who want to learn new skills and build a solid foundation for working through conflicts and moving forward in ways that strengthen their bonds.

5. Questions for Couples Journal: 400 Questions to Enjoy, Reflect, and Connect with Your Partner

Whether you’re celebrating 30 days or 30 years, Questions for Couples provides the perfect place to dive deep and learn more about each other’s passions, dreams, and relationship goals. It’ll also help you explore your memories and values, and how to create a fulfilling life together that you’ll cherish.

This activity journal with questions for couples includes:

• 400 questions―Browse hundreds of thoughtful prompts to find ones that suit your mood, including telling topics like Your Relationship, Goals and Dreams, and Just for Fun.

• Flexible format―These open-ended, unnumbered questions for couples can be tackled any way you like―and there’s equal space for both of you to record your responses.

• Makes a great gift―Share the lasting rewards of more profound love, deeper understanding, and connection with your partner.

Questions for Couples is a fun, flexible way to learn more about your partner―and your relationship.

 

Conclusion

Asking someone to be your Valentine is a tradition that can bring joy and romance to any new or long-standing relationship. Whether you choose a heartfelt, playful, or creative approach, the key is to make it personal and meaningful. So don’t hesitate—go ahead and ask, and make this Valentine’s Day memorable!