Valentine’s Day. For some, it’s a day designed to celebrate love and connection with your beloved partner, but for others, it’s a day to cry into your pillow and contemplate all of the romantic encounters you’ve ever had. And Valentine’s Day with a situationship? It just gets way more complicated.
Urban Dictionary defines a situationship as “Less than a relationship, but more than a booty call, a situationship refers to a romantic relationship that is, and will remain, undefined.” Sounds about right — basically like a romantic purgatory if you really think about it.
IDK about you, but I’m low-key dreading Valentine’s Day this year. I’ve somehow found myself in a year-long situationship with no idea how to approach the topic of Valentine’s Day. Do I bring it up to him? Do I hope he says something first? Do I just give up and spend the day with my girls? The questions go on.
Maybe you’re like me, and you have no idea how to address Valentine’s Day with your situationship, whether it’s long-term or short. And if you’re struggling to figure out how to spend Valentine’s Day this year, you’ve come to the right place. I got the DL from Relationship Coach Katie Dissanayake and Licensed Mental Health Counselor Jessica Lamar to find out whether it’s really worth spending Valentine’s Day with your situationship this year. And, if it is, how you can do it.
Is It “Worth” spending Valentine’s Day with your situationship?
TBH, this is never an easy idea to approach with yourself; it can honestly feel like mental warfare trying to figure out if you should spend Valentine’s Day with your situationship or not. “If you constantly find yourself questioning where you stand, investing emotionally in Valentine’s Day may not be wise,” Dissanayake says. “However, if both enjoy the current dynamic and have similar expectations, spending the day together might be enjoyable.”
IMO, before deciding to spend Valentine’s Day with your situationship, it might be best to reevaluate your relationship and determine if that’s what you really want to do. Do you really want to spend Valentine’s Day with this special person, or do you just not want to spend the day alone? As Lamar explains, “Valentine’s Day shouldn’t be about proving your importance to someone or testing them on how they feel about you; it should be about celebrating a connection that already feels good because you shouldn’t have to wonder if someone wants to be with you.”
How do you bring it up?
Now, I know what you’re thinking — having to text your situationship and ask if they want to spend Valentine’s Day together might seem like another form of hell, but who doesn’t love someone who takes charge and knows what they want? Plus, if you’ve determined that you do really want to spend Valentine’s Day with your situationship, then this is a conversation that needs to be had, and it’s really not worth waiting and hoping that they’ll text you asking about it.
While it might seem terrifying, mentioning Valentine’s Day can bring a lot of clarity to both parties about what you’re hoping to gain from your relationship (or lack thereof). Lamar explains, “The goal isn’t to trick them into making big romantic gestures — it’s to see if you’re on the same page.”
Whether you want to bring up the conversation by subtly asking how they feel about Valentine’s Day, or by straight up asking if they want to spend it with you, “Bringing up Valentine’s Day in a situationship requires honesty but also self-protection,” Dissanayake says. My advice? Honestly, just go for it; at least you’ll know where you stand.
But what do you do on Valentine’s Day with a situationship?
So, you’ve determined that you’re going to spend Valentine’s Day with your situationship, but WTF do you guys do together? Going out for dinner seems too romantic for someone you’re not dating, but do you really want to spend your Valentine’s Day having yet another “Netflix & Chill” night? According to Dissanayake, “The key is ensuring both people are on the same page.”
Keeping your day with your situationship “fun and low-pressure” is the best way to acknowledge the day without going “full rom-com mode”, as Lamar explains. Whether your idea of casual is ordering takeout or going out and grabbing drinks, there are so many ways to spend Valentine’s Day “in a way that feels good for both of you,” says Lamar.
OK, But should I give my situationship a gift for Valentine’s Day?
My personal answer would honestly be “no label, no gift!” but if you genuinely want to give your situationship something, don’t let me stop you! However, “if you’re expecting a gift in return or hoping it’ll push the relationship forward,” that’s when you’re gifting for the wrong reasons, Lamar warns. “Give because you want to, not because you’re hoping for something back.”
That being said, something small, but thoughtful, honestly seems like the best way to approach gift-giving with a romantic partner that you’re not quite dating yet. Giving a gift that’s too romantic or sentimental “can create pressure or misaligned expectations,” Dissanayake reveals. TBH, a playlist, their fav midnight snack, or something relating to an inside joke, is a great way to play it safe regarding gift-giving, Lamar advises.
How do I approach the “what are we” conversation?
So, you’re seeing all of the heart decorations and boxes of chocolates in practically every store you walk into and it’s making you feel some type of way. While I’m sure you’ve been tiptoeing around that “What are we?” question for the past few weeks, scared of what the answer might be, now is honestly the best time to ask it.
“Rather than framing it around [Valentine’s Day], express what you genuinely need in a relationship,” Dissanayake emphasizes. It’s important to figure out what you really want first before having any serious conversations. Is the idea of Valentine’s Day just making you wish you had a SO, or are you genuinely ready for, and wanting, a relationship?
While it might seem scary to ask that ever-so-feared “What are we?” question, it’ll honestly give you the clarity you need to move forward in life. Whether you want to pose it as a simple “Where do you see this going?” or a straight-up “What are we?” it’s important to brace yourself and understand that you might not get the answer you’re looking for.
But what if they don’t want to spend the day with me anyway?
Picture this: you ask your situationship if they want to spend Valentine’s Day together, fully expecting that they’ll say yes, only for them to reject your offer and say no. Um, what now? While it might sting to hear, it can honestly be freeing, Lamar says. It just shows that this person doesn’t see your relationship the same way that you do, which def sucks, but “now you can put your energy toward something (and maybe someone) that actually aligns with what you want.”
At that point, “it may be time to reassess whether [your situationship] truly meets your emotional needs,” Dissanayake reveals. If it doesn’t, don’t be afraid to make plans with your besties, and hey, maybe you can end your Valentine’s Day with a little self-love too.
Overall, figuring out your Valentine’s Day plans should never be this complicated — if you’re finding yourself overanalyzing whether they deserve a Valentine’s Day date, they probably don’t. And worst comes to worst, don’t be afraid to smash some plates at a rage room with your besties so you can make sure the only thing breaking this Valentine’s Day is some glass (and not your heart).