7 Questions About Dating You Wish You Could Ask


1. Why don’t people call back after an awesome date sometimes?

You cannot ask this because you already know what the answer is, and you don’t want to hear it. The truth is simply that what, for you, constituted one of the ~best dates of your life~, was pretty uneventful for them. They just don’t like you as much as you like them. So it’s much easier to spend the next two weeks coming up with increasingly absurd rationalizations for why it has been taking them so long to respond to you, culminating in a screeching delusion about how they had died in some horrible accident on the way home and their last breath was used to cry out “Tell that girl that I really liked when she put her hand on my inner thigh during the movie. Tell her I totally would have called her again and worn looser pants next time!!” before collapsing in a pile of their own blood.

2. How do you actually declare that you are dating?

We really didn’t appreciate what we had when we were in middle school and you just kind of went up to someone and were like “we are boyfriend and girlfriend now” and then proceeded to demand a strict regimen of hand-holding in the cafeteria for the next two weeks, until you promptly broke up with them by doing the same to the next unlucky suitor. Now, it’s all some kind of Smash Brothers Melee where God only knows what everyone else is looking for, and who else they’re seeing, and how they feel about you. Asking someone “Okay, are we exclusive now?” when it hasn’t been made perfectly clear already is akin to diving off a cliff with a bungee cord you bought in the back of a consignment store, but there seems no less risky way to go about it.

3. When is it appropriate to start integrating friend groups?

There comes a point when you are dating someone you really, really like and you are really, really excited that they’re a part of your life, and you want everything to just go perfectly. You then proceed to look over at your group of friends who, when they are not transmitting friend-exclusive STDs to one another, are generally being humiliating and scouring the city for two-dollar pitcher nights like aquarium suckerfish. You imagine their friends, who are no doubt young hotshot philanthropists with really good hair and diversified stock portfolios who like to frequent jazz clubs in their spare time. You think about when you’re going to have to start bringing this perfect new person into your fold, and you cringe. Too soon, they’ll be scared off. Wait too long, and they’ll assume that you are a cave-dweller whose friends largely exist on yaoi forums on DeviantArt. It’s an impossible balance.

4. What does it mean if you don’t actually go out on “dates?”

What happens if you are the person who just mostly starts their relationships by moving from the friend/party acquaintance phase into the “we are sleeping with each other on the reg, guess one of us should put a metaphorical ring on it at some point” phase? What happens if that is you? Is there something defective about you because you are not the person who goes out to a reasonably-priced Thai restaurant, holds hands nervously on the way to the latest Woody Allen film, then has a chaste kiss in the back of the taxi before swiftly returning home to blog about it whilst getting your hand stuck in a near-empty tube of Pringles? It seems like a fundamental human experience.

5. Is there such a thing as “too many dates?”

On the flip side, and speaking as someone who has spent their share of time on “let’s-not-admit-this-to-my-grandmother-who-doesn’t-understand-the-internet” dating websites (I think she would think “dating website” means “cybersex”), there can come moments where you are stacking up your dates like some kind of fickle little millefeuille who is quickly running out of “going out” clothes. When it comes to the end of your third date in as many days that has largely consisted of staring blankly across a table of fried pickles and craft beer, wondering how rude it would be to check your phone again, you come into a bit of an existential crisis. Are we just dating because it’s easy to go out with someone, and is it numbing us to the magic of a night out with someone you really, really like to be accepting dates just because the profile picture was well-lit and their reading comprehension surpassed an eighth-grade level? Is it too easy to go out with someone? Maybe, but all of this becomes null and void if the date on the fourth night proposes to take you out to Dave and Busters. It’s like Chuck E Cheese, except you can get wasted.

6. What do you do if your friend is dating an asshole?

Hire a drifter to kill them and make it look like an accident? That seems like the only reasonable answer. It really feels like the most humane option, anyway.

7. At what point am I the problem?

This is truly the question that no one is allowed to ask because the answer is just too bleak. Like, none of your friends are going to turn to you after you finish your zesty monologue about the latest dating prospect to disappoint you in every category and be like, “Umm, no, the real source of your problems is a combination of your refusal to be introspective about anything other than what degree of spice you want to get in your queso at the grocery store, and your affinity for dating people who remind you of all of the family members you avoid at holiday gatherings. You should just get a pet that can’t run away too quickly.” That is a discussion you have to have entirely with yourself, and nothing is more terrifying than realizing it may be overdue.

Just kidding, soul-searching is for ugly people and liberals. You are way too perfect for that. Thought Catalog Logo Mark


Chelsea Fagan founded the blog The Financial Diet. She is on Twitter.

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