1. “Am I being carefree enough?”
Whether you realize it or not, when dating someone new, women are constantly straddling this weird line of whether or not they are being carefree enough or not. If we seem too interested, it could be a turn off. If we aren’t interested enough, he might not know we’re into him. It’s this ridiculous back and forth of trying to seem interested and trying to seem like we don’t care and, in the end, it’s so much disingenuous effort that we wish it didn’t have to be a consideration. It’s like there’s this fantasy world where everyone brashly states their intentions and nobody has to appear as anything except as they are and we all would like to get to that place, but nobody knows how to get there.
2. “Did I sleep with him too soon?”
When has a man ever in the history of his life asked himself if he slept with a woman too soon, maybe so soon that she will not be interested in him anymore. Never! Never has a man considered this. Yet, it might be the chief consideration among women. When is the right time to have sex? The timeline of when a woman agrees to have sex with a man is riddled with meaning for both parties involved. Why can’t it just be the time when it feels natural and right? Why does this have to be such a big deal that can make or break the potential for something real? Sex is a big deal, of course, but the fact that intentions and expectations cannot be communicated in modern dating is seriously making everyone a little bit psychotic.
3. “Am I being crazy right now?”
In modern dating, no word is more feared than the c word. CRAZY. Once a woman is deemed “crazy,” it’s over. And, the worst part is that we have no clue as to what will label us as crazy. Will it be that we texted two times in a row? Did we mention anything that would give the impression that we were not, like, “totally cool” with whatever? As women, we have to straddle the 3 c’s: cool, carefree, and crazy. We have to be cool enough, carefree in all the right ways, and definitely never ever ever ever crazy. Too bad we have no idea what gets us brandished as a “crazy girl” because it varies from man to man.
4. “Should I text first?”
There is perhaps nothing more fraught with horrific deliberation like what message it sends to initiate a text conversation with a guy. What will he think? Will he think I’m too eager? Will he stop being interested if I say “hi” today before he does? WHAT DOES IT MEAN? WHY DOES IT MEAN ANYTHING? The fact that we can’t just text at will without first having to consider the implications or consequences of that first text is, maybe, the most frustrating part about modern dating. Why does it matter who initiates the text? Why does it have to mean anything at all?
5. “Is he going to be turned off if I ask him out?”
People are always saying, “Just ask him out, it’s a new age!” Yeah, that’s a really great thought and, in theory, seems awesome because equality! Yet, we still have to consider whether or not that particular guy we want to ask out is going to be turned off that we made the first move. Which, of course, could mean that person is not for us, but it’s still this ridiculous thing we have to consider back and forth. Men are afraid to talk to a woman because of the potential for rejection and we are likewise afraid of rejection, but are also considering the possibility of ruining our chances with a guy by simply showing that guy we are interested in him. How does this make sense? Somehow it does in our modern dating world! 
