A Suggested Timeline For Revealing Your Crazy To A Guy


One of the biggest questions when it comes to dating is when exactly to reveal “your crazy” – ie. show a guy your worries, neurosis, insecurities, and all of the other parts of your emotional makeup that may send him running scared. Personally, I’m a fan of just putting all of the crazy out there up front, but not everyone subscribes to that level of openness at the beginning of a relationship. So if you’d rather take your time in revealing the true you, here’s a timeline that may help you out.

Before The First Date:

Depending on how you meet, the period before Date 1 may be very important. You want to seem as normal and carefree as possible. He doesn’t text you back? No problem, you didn’t even notice since you were busy with the “girls” (aka Netflix and a pint of ice cream). Cancels plans? Totes cool, you really wanted to go to fajita-and-margarita night with your bestie anyway. Everything is easy-breezy.

The First Date:

Perhaps it’s a casual meet up for coffee or drinks, or maybe something a little bit more formal, like dinner. Whatever the venue, the first official date is his in-person test of your level of crazy, so you need to strive for moderation here. Let’s use your drink order as an example: if you order shots, you’re a straight up cray-cray bitch who will likely get drunk this coming Saturday night and show up outside his window. Water, you’re a total prude who is never ever going to let him do butt stuff. A glass and a half of the middle-priced wine? You just hit the sanity sweet spot.

The Second Date:

Well, he didn’t ghost on you after date one, so congratulations! But before this goes any further, you need to test his crazy tolerance. You don’t want to put all of this effort in for months only to have him freak out when you finally reveal your true self. The way to do this: tell a story about “your friend Kendra,” who totally freaked out when her boyfriend went MIA and didn’t text her for thirty six hours. A WHOLE DAY AND A HALF. Of course, there is no Kendra; this story is obviously about you and what happened with your last boyfriend. His reaction is going to tell you exactly what’s going to happen when he forgets to text you during his golf weekend next month.

The Third Date:

We all know what happens on the third date, right? It may be time to let your (sexual) freak flag fly – within reason. You’re into some light spanking and dirty talk? I’m sure he’s gonna be cool with that. You want to have a gang bang with him and twelve of his fraternity brothers? He might be cool with that too, but you should probably build up to that.

The Fourth Date

So he’s still answering your texts after the big event? Props to you. He’s clearly into you, so it may be time to start letting him in on a little bit of your craziness by asking him some simple questions, such as who that girl is in his profile picture or what he did last night. Subtle, but just enough to let him know you’re paying attention – and he’s not going to get anyway with anything.

Dates 5-13:

You keep it moderately cool through the next series of outings. Still not quite sure if you’re committed or not, you try and keep it casual. Sure, you drop little hints here and there, but you’re totally chill with just taking your time and seeing where it goes.

Date 14:

It’s been a few months, a few actual dates, and a few sex sessions and you’re starting to wonder what the deal is. Is it okay if you are still talking to/banging other dudes? Is he still out there looking? Why the fuck does his Tinder profile say he was active 20 minutes ago? You start asking yourself all kinds of questions – ones that you know you can’t ask him without sounding batshit crazy at this stage of the game. So you casually bring up your status, jokingly, and try to keep your reaction neutral when he sidesteps the question.

Date 15:

You’re starting to get a little bit confident. There’s a certain strut in your walk, a twinkle in your eye, and a hook in the guy. So much so that you are starting to think that maybe, just maybe, this could be it. You aren’t stupid enough to show him your secret Pinterest wedding board quite yet, but mentioning that you’ve always wanted a fall wedding is totally normal, right?

Date 16:

Oh, no. You feel it welling up, like the tears you can’t hold back at the end of The Notebook. You’re trying to hold it in, but sitting across the table from him at this moderately priced restaurant, you just… can’t. “Where were you last night? Why didn’t you answer my text? Why did you call me ‘your friend Jenn’ when you were on the phone with your mother? Are you still banging other girls? WHAT THE FUCK ARE WE?”

Post Date 16:

Oh shit, oh shit, oh shit. You both survived dinner – him by trying to calm your fears and you by knocking back a bottle of Moscato. He was kind, but when he dropped you off, you’re pretty sure he laid rubber peeling down the street. You’ve texted your apologies for your full-on psychotic break, and he didn’t answer (probably because he blacked out trying to drink away the memory of your head almost doing a complete 360 on your neck, Exorcist style). So now you’ve moved onto the “This is who I am, take me or leave me,” tactic. Guys love confidence, right? RIGHT?

Date 17:

Oh, who the hell are you kidding? You’re never seeing that guy again.


Email this to a friend

Jenna Crowley

Jenna used to be known as 2NOTBrokeGirls, but then one of the girls actually went broke, so she's struck out on her own. Jenna spends her free time saving the world, one sorority girl at a time (usually while wearing yoga pants), questioning why she decided to get a doctorate, and documenting her love of all things cheese related. You can ask her anything you want about football, using your boobs to get what you want, and pizza at @JennaLCrowley on Twitter or via email at

For More Photos and Videos

Latest podcasts

New Stories

Load More