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

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

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

— Kiana*, 23

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

— SpiritSoul88 on Reddit

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

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

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

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

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

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

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

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.