Does Being "Chill" While Dating Actually Work? 13 People Explain Why It's Not For Them

It's easy to look back to centuries or decades past as quaint eras of dating. But TBH, a lot has has changed even within the last five years. One of the main shifts has been toward keeping things "chill" — that is to say, ambiguous AF. "Situationships" and (all the other newfangled words and behaviors that accompany undefined relationships) are the norm. It's all about going with the flow, lingering in the grey area, and embracing it, even though you secretly want commitment and the labels. So, does being "chill" while dating actually work? The short answer: "No."

Yes, being "chill" can mean being carefree and having an easygoing attitude, both of which are super valuable traits when it comes to dating. But for the most part, chill dating mostly consists of undefined relationships where people aren't communicating what they really want out of the situation.

As author and dating coach Diana Dorell told Elite Daily, "There is a lot of fear of appearing too eager or desperate for expressing feelings, so the pressure to 'chill' is there." So you or the other person goes along with it, even though they're not happy. And you don't speak up for what you want out of fear — it's a vicious cycle. Here are 13 other people in their own words as to why "chill" dating just isn't the move.

Something's got to give

Javier Díez / Stocksy
Honestly, I believe it doesn’t work out because you either end up catching feelings and the other person doesn’t reciprocate those feelings, or it can lead to more than that — and you end up wanting to be together, for real.

— Kristen, 22

Status: It's Complicated

Some people just aren't comfortable being intimate with people they don't have feelings for, and there's nothing wrong with that. At the same time, you can't hold it against other people if that's what they're into. We all have different preferences!

— jamjhonjam on Reddit

Chilling out backfired

Alto Images / Stocksy
I completely gave up on pretending to be chill because (1) I am not chill, and (2) I had a really frustrating experience that was the final straw for me. After a few months of dating a guy exclusively, I wanted to use 'boyfriend'/'girlfriend' labels, but he kept dodging my conversation about it. Rather than talking to him about our feelings like the two adults we technically were, I dropped the subject and let my resentment toward him grow.
When we hit a rough patch in our relationship, I didn't know how to deal with it without seeming clingy or needy, so I wound up playing games. I texted him way less often than I used to, and I played hard to get when he did invite me out. I thought I was going to get my point across, but he eventually stopped answering my texts at all. When I finally confronted him about ghosting me, he accused me of ghosting him. That was not my goal at all!
I thought being chill would get him to finally like me back, but it just pushed him away for good, and wound up hurting him in the process. In hindsight, the entire stupid situation could've been avoided if we had just communicated honestly and been a little vulnerable with each other.

— Hannah, 26

It's messy

It's not great. You never have inner peace — either commit and be exclusive, or be open and keep it casual. Situationships are messy.

— Kiana*, 23

It will only lead to heartbreak

Someone usually ends up with a broken heart and it sucks.

SpiritSoul88 on Reddit

Sometimes, you can turn a situationship around

Shutterstock
This is how I ended up with my boyfriend! We met in London when I was studying abroad and at the time, I was still 'talking to' someone back in the USA (who I had been hooking up with). I had just gone through a horrible breakup, so when I met my now-boyfriend, we agreed it was just 'chill.'
We started hanging out a lot and going on dates to museums and to get coffee, but we were both also still sleeping with other people. Then, we continued to talk casually all summer and, when we got back to school, started hooking up with other people (and also each other). But it became so stressful.
We were constantly mad when the other spent time with someone else or slept with someone else, and our beautiful, casual relationship became a messy, jealous problem. We had to have a lot of sit-down talks and it took a while to get to the point of hardcore dating. Hut now we are and have been for two years and just moved in together.

— Alex, 23

But otherwise, it's emotionally draining

Oof. Was in one last year: We were together constantly, and were texting and snapping whenever we weren't, kissed and held hands in front of each others' friends, and basically did all of the 'relationship-y' things. Only issue was he wasn't willing to commit, but grew extremely jealous and questioning whenever I would talk to other guys.
[In] all honesty, it was one of the most emotionally taxing things I've ever experienced. And while we're still on good terms and I have no hard feelings, I would never get myself into a situation like that ever again, especially since I do want a serious and committed relationship.
In my opinion, if such a situation were to occur: stay friends with benefits before emotional attachment occurs, get into a real relationship if you know feelings are mutual, and cut ties otherwise.

ayylmaos17 on Reddit

You don't get the trust and intimacy you might need

Lucas Ottone / Stocksy
I can't casually date. I can't be open and vulnerable, and share my body with someone I don't have a deep connection with.

bunsaholic on Reddit

Lack of commitment can really hurt if you're genderqueer

It’s trash because people still have a perception that the world is so black and white. And then there’s people that want to 'try' dating non-binary folks just for the experience. Personally, I have such a hard time flirting or asking someone out because of all of these [identity] labels we got going on.

— Lashelle, 23

It feels like a waste of time

I eventually realized as I got older that casual dating, relationships with expiration dates, [and] casual sex is really just a waste of time, and an unnecessary risk. Once you reach a certain point as an adult, you stop feeling like you have all the time in the world to burn, and instead you have a ton of interests and responsibilities. And it's impossible to justify spending a weekend just f*cking someone you'll probably stop talking to in a few months.

Iamnotyour_mother on Reddit

There's always a longing for the other person

Shutterstock
I’m currently in one with one of my closest friends. We’ve done it all and at one point, he even told me he liked me. He lives in a different state though, because he’s in the military, so we usually see each other once or twice a year.
It just sucks because in a perfect world I know we would be together because we both have feelings for each other. But [neither] of us want to do long-distance and we also don’t want to lose our pre-existing friendship.

graceem on Reddit

Sometimes, it is what it is

I was in one of these 'non-relationship relationships' for a few months. We went out on dates all the time and introduced each other to our friends. While I wouldn’t want it now, it was exactly what I needed at the time.
The guy was very nice, social, and fun, but we had very different lifestyles, goals, and priorities that would have made us incompatible long-term. I was only on a temporary assignment in this city for work, so I didn’t want any sort of commitment.
The 'situationship' allowed us to have fun together without the expectation of a future. When I left, we hugged and basically said see you never!

danicakes on Reddit

Other times, it's a learning experience

Cinemalist / Stocksy
At first, not defining the relationship wasn’t an issue for me. It was something new and exciting, so I didn’t mind going with the flow. But my partner and I have been casual for eight months, without clear communication on what this relationship is or where it’s going. I’ve learned that this type of relationship isn’t the best for me. I have to know how my partner is feeling — and they have to know how I feel — and we both have to be okay with the boundaries of the relationship.

— Brielle,* 23

Unfortunately, when you're too chill, Dorell explained, you are "at the mercy of the other person and [the] circumstances," All of the confusion and the heartache could have been cleared up if you and the other person had just taken personal responsibility for your experiences. And the bottom line is that more than losing your autonomy in the situation, you're also just not getting what you deserve! That's not fair to you.

“Ask yourself if you are holding back and accepting certain behaviors that really warrant a red flag in the name of being ‘chill,’" Dorell adds. "Like someone being an hour late to a date without communicating why."

Situationships can work for some people — and even if they don't work, they can be turned around. But for the most part, if "chill" means ambiguous or passive instead of standing up for what you want? "Chill" dating just ain't it.