Questions to Ask Yourself After a Date

Is he the one?…who cut in line at the Starbuck’s bathroom two weeks ago?


I went through a phase during winter — partially to bulk up anecdotes for Man Repeller, partially to temper Vortex doldrums and mostly because sometimes a girl’s gotta do the damn thing — where I was going on a fair amount of dates. You can hang on to the slow clap though, because a lot of my friends, both guys and girls, were doing the same exact thing. It was like everyone got bored at the same time. Or maybe Groupon was just really hooking it up with the two-for-one-plus-pasta-dish-drink-specials and we got sick of using those on our pet fishes. I don’t know. But amid the mass dating phenomenon, it seemed we all had one common thread: the post-date interview via a barrage of texted questions from our fellow inquiring friends.

The five most common were always:

1) “Did you have fun?”

2) “Do you like him/her?”

3) “Did he/she offer to pay?”

4) “Did you makeout after?”

and 5) “Did you more-than-makeout after?”

These were reasonable at first, and easy to answer:

1) Sure I had fun.

2) Um yea, I like him okay — wasn’t aware he had an attached twin that negated a backslash-her situation, but that’s fine!

3) He paid.

4) No, awkward hug/cheek kiss.

5) See #4.

But then the Qs got monotonous. Routine. And they inadvertently became my own measure of what constituted a successful date and therefore, a small but relevant source of anxiety. (For example, my friend Devon once asked if a date of mine ordered appetizers. His reasoning was that if he likes a girl, he orders apps to extend the date. Going forward I will now have a quiet panic attack and probably sit like a paralyzed goat the next time a future date doesn’t suggest we split a fig. Then I will dread the inevitable question: “So, did you guys get apps?”)

This isn’t to say that our journalistic tendencies should evade us. Asking the hard-hitting questions are always important. I just feel there are more pressing issues we can ask ourselves — or more interesting topics we can quiz our friends on — regarding post-date feelings.

My friend Laura pointed out that one should always ask herself, “Was my hair parted correctly during the entirety of the evening?” Anxiety-provoking? No doubt. But the reason he didn’t ask for a second date? Absolutely.

Another crucial question she routinely explores: “Was the person who just walked me home — aka he now knows where I live — potentially, or definitely, insane?”

That seems reasonable. Reasonable and fun!

I frequently ask myself: Did that individual, regardless of solid manners and a polite disposition to the waitstaff, have an annoying tick that will later cause me to stab him with a shard of glass?

What about: who told better jokes?

Forget the old, Did he have clean fingernails and non-square-toed-shoes? curveball and instead opt for: Is he or is he not a future member of the United Association of Desk-Gum Collections? Followed up with: And am I into it?

Is her middle name Danger? Or even more intriguing: Does she have a middle name at all?

Did he suggest you split a burrito, and then eat your half of the burrito?

These suggestions sound like a joke, and since my brain is involved, they kind of are. But wouldn’t you rather spend more time hanging out with the aforementioned pet fish than waste energy agonizing over whether or not you had kale in your teeth the whole time, or just at the end, and whether or not his drink order-to-bathroom-time ratio signaled his second-date intentions?

No? Ok. I get it. Pet fish are kind of lame. So instead why don’t you tell me: what questions should you ask yourself/do you ask yourself — or your friends — after a date?

Original image shot by Chris Craymer for Glamour UK, February 2013.

Get more Postmodern Love ?
  • Same thing happened to me this winter. It got exhausting. Great story material, though. So now questions such as: did he show up, did he spit out his arugula, did he show up drunk, did he wear a backpack, did he tell you about his porn collection, did he tell you how much his dad makes in a year, were ALL of his tattoos claiming God doesn’t exist, how many times did he ask you about your 401k seem normal now.

    • Amelia Diamond

      …did he tell you about his porn collection? a guy once made me split a burrito with him and then ate it. actually i’m going to go add that in now.

      • HAHAHA. Did you at least get any chips and guac? Did he order jumbo shrimp from the raw bar portion of the menu expecting $3 to be the price for unlimited shrimp? then yell at the waitress when he found out jumbo shrimp are $3/each?

      • Charlotte Fassler


  • Kandeel

    “Was the spinach stuck in my teeth the whole time?” edit: i just finished reading the article and you already said that. Dammit Amelia!

    • Amelia Diamond

      well i said kale; spinach is an entirely different beast. worst: the poppy seed.

  • rdizzle

    Did he tell you he hadn’t had sex in a year and a half, and then straight up proposition you? Five minutes into the date?

    True story.

    • Amelia Diamond

      oh wow.

      • rdizzle

        I couldn’t help it, I cracked up laughing. Poor guy =)

        • Trente Chic

          the worst is sharing tinder profiles and him showing you all the girls he’s currently talking to and going out with next…

  • Q’s to ask yourself: Was that a natural musk or was it store-bought? Because DAMN I have never smelled someone so manly. Was he overcompensating for something? Why did he hold his silverware like that and would I be able to sit through that for the rest of my life? Did he stalk my social media as extensively as I did his?

    Q’s to ask ya friends: On a scale of 1-10 how much does he belong in the Vampire Diaries? What I’m wondering is if he looks like he was sculpted by Michelangelo. Did you get a look at his foot size, because, well, you know the saying. Were his eyes murder-y or gingerly? Why would he take you to a Korean facial place on your first date?

    • Amelia Diamond

      BAD SILVERWARE HOLDING = kod. kiss of death.

  • starryhye

    Did I opt out of the dating game too early?? These comments are hilarious! Albeit probably not so funny for the person on the actual date…Cheers to all you ladies (and fellas) braving this crazy dating world.

  • Nathalia Kalil

    Good questions! We gotta be happy!

  • Natalie

    Fabulous article, i went through this last fall and the people I encountered really made me question myself tbh. Now I have to ask, did he tell you that he wears “spanx like tanks” all the time to pull off a slimmer look? Did he tell you that he speaks in religious tongues when he prays? If the answers are no, then at least I can stay for another drink.

    • Amelia Diamond

      spanx like tanx??

      • Natalie

        Spanx like tanx. And no sir, I do not want to touch them..

  • LadyMary

    Here’s my question for myself after I finally meet someone in person after exchanging a few lame perfunctory emails via OKCupid ….

    “Do I want to go out with him again next Saturday night ? ”

    – OR –

    “Just stay home & watch a Downtown Abbey rerun ?”

    (Guess which option usually wins… sigh*)

    • Amelia Diamond


      • Trente Chic

        I just opted out of going to BLT Prime to watch True Blood

  • BethanyBeach

    I think the most important question is if he appreciates puns, because he’s essentially out if he doesn’t.

    • Amelia Diamond


  • Lyric

    Did he compare you to looking like a guy because of your pixie cut, but as a complement because he’s bi and “into guys too”?

    No? Just me?

  • Hilarious and the comments are just as funny!

    • Amelia Diamond

      haha i know i’m cracking up reading everything you guys are saying!

  • Regina

    Oh there are tons of questions I used to ask myself. Am I ok with him criticizing my wine consumption after revealing he doesn’t drink at all? Or is it permissible for him to show up with an alarmingly overgrown beard after claiming to be too lazy to shave upon returning from Costa Rica? Maybe he was turned off by my impressive appetite…or possibly my rampant sarcasm…I’ll never know I guess, but I know I’m better off!!!!

  • Jane
  • Charlotte Fassler

    Did I drink too much? What did I say? yikes.

    • Trente Chic

      this is every time…

  • Leah

    Did he try and top every funny anecdote I had with one he thinks is funnier and better? It’s a date, not a competition. Get lost.

  • Gimme Dat

    Did he invite you to sushi, show up with wet hair, and then tell you he had $20 in his bank account until Friday?

  • Alexandra Puffer

    Let’s focus on: Did you laugh? Would your momma/best friend/grandmother like his company for a meal? Did he compliment you?

    Dating SUCKS. Good luck!

    Warm Regards,

  • Julie

    I always ask myself:
    1.) Was I laughing because I really thought he was funny, or was I just trying to make it less awkward?
    2.) During the date was my mind on other things, if so was the date not interesting enough?
    3.) Do I naturally feel comfortable being myself with this date, or do I feel the need to act/look slightly different?
    4.) When I evoke the physical contact, is it because I feel like I should, or is it because I want to?

    • Zoe C

      these are going in my notes

  • Allison M

    What not to do on a first date: Tell him he sounds like a sociopath because you just finished the book “Confessions of a Sociopath” and are hyperaware of sociopathic tendencies and qualities. Whoops.

  • True first date story:

    After my date orders guacamole for us,

    the waitress asks us: “how spicy would you like it?”
    My date quickly answers: “spicy, very spicy”
    Side note: I like mild!

    True first date story #2:
    Him: “so what sign are you?”
    Me: “scorpio, you?”
    Him: “Scorpio. Me too. Should we even bother?”

    • Trente Chic


  • QC

    The scene: first date drinks date in a low light (aka atmospherrrreeee) bar. My date: “What about acne. Do you have acne?” *Oh dear*

    • Trente Chic

      FML seriously?!?!

  • Isadora

    Most recently I find the pressing questions I have been asking myself are- can you get over his dangly skull nipple piercing? Did you get home to find you had part of a black bean stuck between your front teeth, having only eating bean related items fairly early on in the date? or better yet, how do you feel about a second date after having to sit next to him and his ‘tinder date after you’ in a far too cozy pop up restaurant on a communal table, both trying to pretend its not happening? you know, just the basics really…

  • grownup

    Late to reading the article but how about: was he 25 minutes late picking you up for a dinner date because he was busy creating and posting a video of himself working out to instagram?

  • drink order to bathroom ratio


  • Scarlett

    Does he have a Probation Officer? Does he have baby mama drama? Does he live in a small two bedroom apartment with his grandmother, and claim(like a wannabe Thoreau) that paying taxes is wrong? Not all in the same date, but questions, I have added to my list since they spring the answers on me without any inquiry from my part into the matter.

  • Savannah

    Recently my friends have asked me after a first date: ‘Did he talk shit about his ex and starting crying?? Or did this one actually understand the unwritten laws of dating?’

  • Aditi Mayer

    Did the date lag for 4 hours and end with an awkward hug, followed by a text 2 minutes later blatantly saying, “I wanted to kiss you so bad.” WHAT

  • Willa

    Just one question really.

    Is he my kind of crazy?

  • “can he be a THE father of my futur kids” is the pathetic question i can’t help but wonder all the time!!
    But you shouldn’t, its most of the time a killer….

  • Zooey P

    my friends just check in to make sure I’m alive. stay sexy – don’t get murdered

  • Noelle Smith

    I know I shouldn’t make fun of how people talk but I went on a date once with a guy who legit talked like Elmer Fudd..all his R’s were W’s…so distracted for the entire date just listening to him talk ( A LOT)

  • Antillanka

    (I was driving us to the restaurant because I really don’t mind, I don’t drink)

    Did he make you wait for 10 minutes out of his place and then got on the car still not completely dressed, without giving any kind of explanation?

    Did he instructed every freaking turn to you even if you hinted him maaany times that you knew the neighborhood like the palm of your freakin’ hand and didn’t need any directions at all???

    Did he start talking to the staff in (terrible) french after he drank a bit too much?