How to Handle Valentine’s Day When You’re in a New Relationship

How is it that you’re supposed to celebrate Valentine’s Day with someone you just started dating? Couples face this question every year, and if you’ve recently begun seeing someone, you both are probably starting to have questions about the upcoming holiday. Whether you call him your “kind of boyfriend,” “this guy I’m seeing”, or your mythical Tinder date gone right, figuring out how to approach Valentine’s Day is stressful for a lot of us, especially during the dating vs. relationship grey area. With these tips, you can tone down the awkwardness of the occasion and make for a great first Valentine’s Day together.

Valentine's Day

By Holly Tomlinson

Communication is Key:

You’re going to have to actually talk to him about it. I’m not talking about a drawn out round table discussion here, but determine a way to have a casual conversation about Valentine’s Day. Guys are under a lot of pressure during Valentine’s Day, and he may be wondering if making plans will scare you off, or he may be nervous about doing something too serious too soon. Your best option is to be direct. Ask him what his thoughts are, and make sure you two are on the same page as the date draws closer.

Be Careful with your Expectations:

This is a new relationship, and you need to have realistic expectations. Don’t expect a horse-drawn carriage, hundreds of roses, and declarations of undying love. Your expectations may be different if you’ve already set plans for the evening. If you do have plans, think of this as just an extra special date night. If you don’t have plans together, don’t expect a surprise appearance.

Gift Exchange:

If you two are exchanging gifts — and you should discuss whether or not you want to do this if you’re at the point where it’s comfortable — my best advice is to stay thoughtful. No crazy expensive purchases (he’ll feel awful if he doesn’t do the same, and let’s be real, so will you). Think about his hobbies and interests, and pick an inexpensive gift that will play to them. Perhaps it’s a concert happening the next weekend (avoid buying tickets to anything too far in advance, as this places more pressure on the two of you to make it work until that date), or maybe it’s an experience gift like go-kart racing. Whatever you decide on, keep it light, keep it fun, and cater it to his interests for a foolproof gift that he’ll definitely appreciate. If all else fails, keep it inexpensive and classic with some chocolate dipped berries.

Make Your Own Plans:

If it’s looking like you two won’t be hanging out on Valentine’s Day, stop the inclination to worry. Make other plans and celebrate the diverse loves you have in your life: Your best friends, your sister, your parents, and yes, even yourself. Love is always a good reason to celebrate, so don’t let your lack of plans with a guy get you down. Keeping yourself busy is the best way to avoid disappointment of not going out with your guy, and if you are in a truly new grey area, it’ll cut down on the pressure for both of you if you’ve got other things to keep you busy. Head out to the movies with your single friends for Galentine’s Day, or invite them over and have DoorDash deliver some delicious cuisine right to your door. Skip the crowded restaurants order food and make Valentine’s Day inspired desserts.

A holiday celebrating love shouldn’t be cause for distress, so talk to your guy, and don’t be too disappointed if this isn’t the Valentine’s Day dates you’ve seen in the movies. Focus on all the love you have in your life and make the holiday great no matter who you spend it with.

By Holly Tomlinson. Image via Brit + Co.

14 Responses to How to Handle Valentine’s Day When You’re in a New Relationship

  1. Ashley says:

    I feel like all of these are so important for any relationship! Managing my expectations is my biggest issue sometimes!

  2. Cristina says:

    This is such an important post! My boyfriend and I spent our first Valentine’s Day together when we had only been together for a few weeks. We definitely had to communicate about how we wanted to celebrate, and we even set some guidelines for gifts. (I think we ended up just getting dinner together!)

  3. Jumping into a relationship just before Valentine’s Day has actually happened to me twice…the first time was when I was 16 and my ridiculous expectations left me disappointed, the second time was way better. We talked things out and realized we both just wanted to spend the day with our group of friends, it took away the pressure to be super romantic but we had a great time anyway. xx Merisa | Monogrammed Magnolias

  4. Kayla says:

    I totally think these are valid points for any relationship — regardless of how new it is!

    Kayla || Keynotes from Kay

  5. Lauren says:

    Love this! They’re all so true! I think communicating about it is key because then it gets SO awkward.. I’ve had that happen to me!

  6. Kayleigh says:

    My roommate went through this last year! Love the insight on this.

  7. This is great! I’ve been in a relationship for 8 years (married for almost 2), so it’s been a long time since I’ve gone through this, but I can still relate and I think you hit the nail right on the head with communication.


  8. Sockwun says:

    Wow, this is not something that I have thought about, but it is so true that Valentine’s Day for new relationships is super awkward! I experienced this once when my boyfriend-at-the-time and I made our relationship official a few days before Valentine’s Day, and I agree that communication is key! I was just going to ignore it (which was probably a bad idea), but he brought up the conversation and very casually asked me if I wanted to make plans for Valentine’s Day. I said no, but talking about it sure beats making assumptions!

  9. Great tips! The first Valentine’s day in a relationship can be touchy! I think all of these still apply to any stage of a relationship!


  10. Tiffani says:

    These are totally awesome tips! I’ve been dating my man for four years, but before him, I went through my fair share of awkward v-days and other holidays with guys. It’s such an awkward feeling not knowing how you should handle gift giving, hanging out and all of that jazz.

  11. Jordyn says:

    Valentine’s Day can feel super awkward in a new relationship, last year I was so unsure how it would play out in my new relationship. I’m so glad my new boyfriend at the time took the lead!

  12. Nicole says:

    I remember way back when I just started dating my husband. I wasn’t sure if he and I would do Valentine’s Day, so I would have loved this post back then! hahah Chocolate dipped berries really are the best gift and always a winner,

    Nicole // Chronicling Home

  13. This is so perfect because I’m actually going through this right now. There’s this guy that I’ve been hanging out with, but we have yet to DTR, and I’m not sure if we will before Valentine’s Day. I love the idea of going out with my single girlfriends! It’s fun to celebrate love, whether it be romantic or not.

  14. Pingback: Valentine's Day Date Ideas - Elana Lyn

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