There is a lot of advice going around about what to do when you’re single on Valentine’s Day. There’s also a lot of advice for couples.  But there is not a lot of advice about WTF do to when you’re in between. How can you tell? If your response to the question, “Are you seeing someone?” is “Umm…” followed by a long, contemplative pause, that’s a pretty good indication. While there are many advantages to keeping things casual, one downside is the confusion that comes along with it. It’s rough out there guys. It’s like the blind fucking the blind. And when it comes to Valentine’s Day, there is only one word that accurately describes what it’s like for those of us who are in the middle ground: OOF.


Do you ever look at two people together and imagine the horror it would bring to their faces to pop out of nowhere and be like “HEY, SO…WHAT ARE YOU GUYS?”. No one with a soul would do this to two innocent young lovers. But isn’t that exactly what we do to them on Valentine’s Day? Any other time an appropriate response might be, “We’re just having fun. We’re not putting a label on it yet.” Translation: We are fucking and talking, but we don’t yet know what this means.

Even within the “non-relationship” arena, there are sub-categories. For example, with some people it’s pretty clear it’s strictly a “Wam Bam Thank Ya Mam” situation. Whereas other people might engage in casual sex, but also enjoy a meal in public together on occasion. Wherever you & your “sex friend” land in the spectrum, come Valentine’s Day, there is this immediate pressure to pick a side. It’s uncomfortable. You were still dipping your toes in the water and all of the sudden you’re being forced to either swim or get out of the pool entirely. So whether you’re friends with benefits, or in the developmental stages of a relationship (a relationship fetus, if you will), here are some of things that might come up for you, and how to handle them. They will vary depending on where you fall on the “Umm” scale.


This is for those of you who are closer to friends with benefits. While you most likely won’t be spending Valentine’s Day together, the question of “Do we even acknowledge it?” might come up. A lot of time guys have the assumption that when they’re casually seeing someone, any sign of “relationship” behavior and boom, she thinks you’re her boyfriend. It is understandable that they will be unsure about exactly how to handle Valentine’s Day, but hey, that’s why I’m writing this. What they don’t realize is that this assumption stems from a stereotype that all women want relationships, and the ones who say they don’t are lying. I don’t mean to sound bitter, but get over yourself dudes (and dudettes-none of this is strictly applicable to men).

Last year I had just started hooking up with a guy, which was pretty clearly a casual thing. I was just going to go the whole pretending Valentine’s Day doesn’t exist route when I got a “Happy Valentine’s Day” text from him. I didn’t find it romantic, necessarily, but I found it appropriate. It was his way of saying “I am acknowledging that I have been inside of you and I respect you as a person.” I’m not saying you need to send a mass text to every person you’ve ever Tindered, but if you have a “friend with benefits” or even a few people you are currently seeing, an innocent “Happy Valentine’s Day” won’t kill you. It’s simply good sex etiquette.


For those of you dabbling closer to relationship territory, Valentine’s Day will bring up lots of questions. In the early stages of a relationship, there is so much uncertainty on both sides. Women are plagued with, “Am I being used? Does he like me? Am I being slutty if I’m just having casual sex? Is he going to assume I want him to be my ‘boyfriend’?” Guys are plagued with “I like her, but I also like my freedom. If I keep being nice to her is she going to assume she’s my girlfriend? Will she freak out if I tell her I don’t want to be exclusive? Should I just ghost?” And both are plagued with, “It’s Valentine’s Day soon. FUCK.”

While these are generalizations, I do think they are an accurate reflection of the types of assumptions about what’s going on for the other person. On one hand, I think there is value in taking it slow. On the other, two people can only happily coast along in casual bliss for so long, before the need to define it starts to come into play. My advice for Valentine’s Day, don’t let it make you feel like you have to choose all or nothing. But do realize that at a certain point, both people need to be honest about their expectations. The reason Valentine’s Day can be so scary for the “in-betweeners”, is that it threatens to reveal what we deep down know but aren’t yet ready to admit. In other words, sometimes the way someone behaves on Valentine’s Day becomes the catalyst for things to move forward, or to come to a screeching halt. What if you’re not ready for either?


I am not in a position to say whether or not you should have “the talk”. What I can tell you, is that it’s a lot less scary and a lot more powerful to look at it in terms of what you want. When you phrase it, “What are we?”, it’s almost like you’re saying, “What do you want this to be? Because my answer is going to depend on that.” Let’s say a recent movie comes up in conversation at a party. You immediately express how much you loved it, only for the cute guy you’re flirting with to tell you that he thought it was the biggest piece of shit he’s ever seen. Do you respond, “Yea, you know, actually, it wasn’t really that good. I think I was just really bored that day and I was kinda tired when I saw it so wasn’t really paying attention hahahahah disregard my opinion.” (obvious exaggeration, but you see where I’m going) My point is, not having any confidence in the validity of your own opinion makes you look weak. If you had simply responded, “Really? I loved it,” it may not have changed his mind about the movie, but at least you wouldn’t be letting someone else dictate how you should be feeling.

As someone who has battled self-esteem issues my entire life, even overcoming the fear of speaking my mind about trivial things, such as movies, was enough of a challenge, let alone doing it in relationships. It is easier said than done, but I continue to work on it. I got sick of feeling like I had no control, which is what happens when you spend every relationship taking cues from the other person. Finally I realized that it’s about what want, not what he wants. I am not suggesting that this conversation has to take place on Valentine’s Day, but if and when that time comes, this is a more powerful and less vulnerable approach.

“But what if I say what I want and they don’t want that? THEN I’LL BE ALONE!! ” Oh hey irrational fear, sup? This is the biggest obstacle to speaking your mind, the fear of losing someone or something. The truth is, if you want something that the other person is not willing or able to give you, it is a reflection of them , not you. And you’re better off for it. There is also a difference between being “alone” and being “single”.

Do you want to throw a blanket over your head and hide out with Ben & Jerry? Or do you want to throw on a leotard and take pride in being the fabulous, independent woman that you are. (Of course, this is happening)

But isn’t having someone better than having no one? Not really. At least not for me. Of course we can all take comfort in snuggling up to a naked body once in a while, but at a certain point, you have to ask yourself, am I okay with this? Or am I pretending to be okay with this? If you want more of a commitment from someone you are seeing, lowering your standards might keep them around a little bit longer, but you will end up getting hurt.


For me, it is the confusion, not the lack of commitment, that I struggle with in casual relationships. While we can’t control our feelings, with honest communication we can control our expectations. So if you’re sleeping with someone regularly, you owe it to them to tell them what your deal is. Sometimes I have been okay with it. Other times I have not. Guys, let me stress here, this does NOT mean I want a fully committed relationship. It simply means, if you want this parking space, you gotta pay the meter a little bit. You can’t just come and go as you please. (I mean, mayyyybe on Sundays, but we’ll see).


First off, let me just say, congratulations, because in 2014, the odds are against you. If there is one thing I learned from my last relationship, it’s the importance of being in touch with what that actually means to both of you. Relationships aren’t about the title, they’re about the definition.

Valentine’s Day rolled around just as we had been “official” for about a month. So while we had made it to the point of acknowledging that we both wanted to be in a relationship with each other, we never once had a conversation about what we wanted from that relationship.

I have always felt that in an ideal relationship, your boyfriend or girlfriend should feel like your best friend that you happen to have really good sex with, which is what I felt like we had. So you can imagine my surprise 11 months later when his reason for breaking up with me was “I feel like we’re just best friends that have sex.” Me: “Wait…that’s bad?”

He was breaking up with me because what he didn’t want was the EXACT thing that I thought encapsulated the ideal relationship. He was 10 years older, and was looking for more than what I could give. To him, a relationship should be your first and main priority, which I fundamentally disagree with. At the time I was heartbroken, but now I realize that it had nothing to do with me. I was not the “shitty girlfriend” I had told myself I was. In fact, I think I was a pretty awesome girlfriend. Just not the type of girlfriend he was looking for.

Again, this conversation doesn’t have to happen on Valentine’s Day, but I wish that it was something we had thought to do before we entered into a year-long relationship that ended in a painful break-up.

So this Valentine’s Day, try not to focus so much on what you are. Instead, focus on what you want. Whatever your relationship is, at the end of the day, don’t we all just want to do it like they do on the Discovery Channel?


I am a comedian, writer, actress, & also rapper living in NYC. I'm 4'11 so naturally my rap name is T-Spoon. Dating confuses me, so I like to write about it. The way to my heart is probably through fart jokes and puppies. (Here's the part where I encourage you to follow me on twitter @halleratyou)

Write A Comment