The Mysteries of Dating (Explained by Men)

Boys/men/guys/dudes are confusing as hell. Especially when it comes to this thing called “dating”.

I have always been fortunate enough to have many close guy friends. There is something special about being considered a “lady bro” and knowing that your best dude will forcibly remove you from a late night run-in with your ex. But just because I am lucky to call many lovely gentlemen and scholars my best buds, doesn’t mean I understand their dating habits. AT ALL.

So, I interviewed some of my best dudes and some casual acquaintances to answer the questions that all the single ladies want to know in hopes of being able to understand one inkling of their dating thought process. We got the hope*ful* romantic, the realist, the charmer and the f*ck boi.

*Names have been changed to protect the privacy (and swag) of these young men. 


First Date

Go-to first date.

Frank: Activity. Takes the stress off the conversation, and gives you an immediate shared experience to bond over. Plus, I’m 98.7% sure I am not a sexy eater.

Doug:  Weekend lunch date at Vert or some small spot like that. That way you the option to meet up that night if things went well.

Matt: This depends on what kind of girl you are taking on the first date. I typically like to avoid the dinner and drinks option, unless its somewhere interesting where you can grab a specialty drink and some fun food like a charcuterie board. I like to do things that provide plenty of opportunities for icebreakers and keep things from getting awkward. Aquariums, Zoos, mini golf, and things of that nature are ideal. (k, showoff. But yeah, yeah I agree. activities are good.)

Brody: I have a handful of little local bars and restaurants that I cycle through. This way I avoid the staff at my favorite spots from laughing when they meet the third girl that week.

What are your thoughts on Netflix and Chill (on the first date?)

Frank: On the first date? Bold strategy, Cotton. Maybe this is acceptable if we’re “hanging out” but if we’re going to go on a real, datey, date thing, step it up. Hopefully there will be lots of time in the future for N/C.

Doug: That’s fine. But if it’s our first time meeting…slim chance she’s getting wifed. Slim…not none.

Matt: Personally, I have never “Netflix and Chill’d” as a first date, at least not with a girl that I actually intended on becoming serious with. Avoid this unless you’re just looking for a friend with benefits.

Brody: Netflix is chill but Netflix AND Chill is just a lame way to ask your date to bang. First date? If you can bring nothing more to the table than Netflix the first time you meet a woman, you should work on getting cooler; you’re not getting laid anyway.

Boys buy? (on first date? when do you stop buying?)

Frank: I’m happy to treat you to anything and everything (ooooooh really? anything!?), just don’t make me feel like you expect it. Also, don’t read too far into this, sometimes its mostly just awkward to ask for cash.

Doug:  On first date – absolutely. I don’t think there is a timetable on when you stop buying. I think that naturally becomes comfortable.

Matt:  Always. There is no exception to this even if you aren’t looking for anything serious. I usually will let a girl pay after our 3rd or 4th outing but only if she asks. Don’t be a douche and ask her to pay.

Brody: I don’t know why gender really matters. I have the means to buy, so I buy.

Sex on the first date, yay or nay?

Frank: Everyone’s a winner.

Doug:  If you hit it off then yeah. I’m in there like swimwear. But there’s something about a woman that makes you wait. Ideally you should wait.

Matt: Never say “no” to sex, but understand that if things go down on your first date its probably not going to last. So if you’re in it for the long haul, maybe think twice.

Brody: I’ve never let an old fashioned rule get in the way of getting super effing laid.

Should you wait until the third date?

Frank: Have sex when you want to have sex. If I like you, it won’t matter if it’s the first date or the 10th. (But, I mean, don’t just hold out to be a dick)

Doug:  That’s ideal.

Matt: I don’t think there should be a pre-established amount of time you need to wait. If it’s right, it’s right and the chemistry between the two of you will tell you when. Just keep in mind the whole sex on the first date warning.

Brody: And skip having possibly amazing sex on the first and second date? Hard no.

Should you wait three days after the first date to call?

Frank: It doesn’t matter when you call, if I don’t like you – I’ll be annoyed, if I like you, I’ll be excited, but I’m not checking the clock. In terms of when I should call? Here’s what I do: Step 1. Take into consideration how the date went, the other persons’ personality, and how (by what means, and of what content) you interacted before the date. Step 2. Guess horribly wrong.

Doug:  Never even heard of this rule. Plus nobody calls anymore. I guess that’d be a bonus if you did. (OK, hello –  gentleman, if you pick up the phone and call, you get ALL the bonus points.) But I’d probably just text the next day.

Matt: To actually dial her phone number and speak to her over the phone? Maybe. (YES.) I think this should be clearly distinguished from texting however. I had one relationship blossom because the girl was convinced I didn’t enjoy the date and wasn’t going to talk to her again. I texted her (embarrassingly) (not embarrassing, do more of that) less than an hour after our first date to tell her I had a great time and couldn’t wait to see her again and that changed her whole outlook. This obviously depends on the girl as well – texting that quick could spell disaster, it’s all about reading the situation.

Brody:  If you want to call her, call her. If she thinks you’re weird for calling 20 times at 3:00am, well you are weird, and she’s not your babe. “Do ya thang manyne, fuck what they lookin’ at.” – Ice Cube

Digital Dating

Are you using a dating app? Which one? Why do you like it?

Frank: Currently? Nah. Previously? Tinder and Grouper. Tinder is a lot like a trip to Brookstone in the mall; its really fun to browse all the gadgets and toys, but if you’ve ever bought one you know they’re cheap and only fun to play with for a week or so. Grouper (3 on 3 group blind dates) is really a fun exercise to see which of the 6 of you can show the least visible disappointment. One time I got sad drunk and signed up for

Doug: Nope. Tried Tinder for a couple weeks but I’m not about that life.

Matt: Not currently, but when I was it was all about Hinge and Tinder (Bumble is lame). Nothing ever serious came from Tinder, it was mostly just drunken shotgun(think rapid fire) liking people and saying outrageous things to see what people would say. I don’t think anything serious ever came about from tinder. Hinge is a whole different story though. Think quality over quantity here. Think minor league vs major league. I don’t mean that the girls are more attractive on Hinge or more interesting or things like that. I just mean that Tinder is consequence-less in a sense. You can talk to anyone and say anything and it doesn’t matter how it goes. But with Hinge I only ever talked to girls I actually wanted to meet.

Brody:  Ahh, I got a babe so I deleted my apps. Yeah, that’s plural. I have a small collection of dating apps. Whatever.

Do you creep your dates before meeting them?

Frank: Not any closer than 3 car lengths, and never after midnight. Jokes. A little Facebook browsing is probably cool, but don’t over do it.

Doug: Not really. Usually meet through mutual friends so there is already some foundation.

Matt: Hardcore. Want to avoid the crazies

Brody: If you ask me, any dude who doesn’t is just dumb. Or lazy. Do your homework, kids.

Who should be the first to contact?

Doug: The guy but that’s getting old. I appreciate a first contact here and there for sure.

Matt: It doesn’t matter to me. If you are interested in someone say something. If you aren’t, then don’t.

Brody:  Are you serious? It’s 2016. If you feel like calling, you should call.

When is it acceptable to double text? Do you ever intentional wait to text some one back?

Frank: You ever notice that texting has a rhythm to it? Everyone is afraid to respond faster than the other because they don’t want to seem to eager talk, or that they’re not busy doing other really cool stuff. This is stupid, but I’m no trend setter, so text you back in a few.

Doug: That’s tough. I have never felt proud sending a double text so I try and steer away from those. And never in the same day. And yeah I have played the waiting game. I don’t think it helps anyone but I’ve definitely done it. Also, I am an awful texter so half the time I’m just trying to string together some bullshit that sounds remotely interesting…and that can take hours.

Matt: I feel like double texting is a tricky subject and depends on your personality and the personality of the girl you are talking to. If you text a girl “Hey, are you busy this weekend? Want to grab a drink?” and she doesn’t respond then just leave it. She isn’t interested. But if the conversation has naturally ran its course and it dies, and you decide you want to ask her to do something later on that’s totally fine.

Brody:  Everyone has their own style of texting. It’s an art form. If you’re the multiple text to convey one thing type person, rock it. Don’t people have more important things to worry about than text message etiquette.

What are your thoughts on “sexting”?

If the female initiates: super sexy. If the male initiates: skeezy and desperate.

Doug: I’m a terrible texter so imagine my sext game. Nah. She can send them nudes tho!

Matt: All for it. But try to wait until after the real thing has happened.

Brody: Yeah f*ck it, I’m down.

Drunk texting – cool or nah?

Frank: Like that Tiesto song, I too like us better when we’re wasted. Plus, I tend to think it’s pretty adorable if you’re texting me drunk while I’m sober somewhere else. But, don’t needy drunk text, (“do u miss meeeeeee??/? i mis;s uuu!!!1!”) that’s not adorable.

Doug: I’ve done this many times and it has never worked out well so I try to refrain from it.

Matt: Love it. Generally hilarious.

Brody:  I’m funny drunk. So – drunk texting is a go.


General Dating

Best piece of dating advice

Frank: “You’re overthinking it.”

Doug: Don’t worry about these rules. Do whatever feels comfortable. Also personality can go a LONG way in how attractive a girl can be.

Matt: Just be you. Smile a lot. I’ll ask the questions to things I want to find out.

Brody: Idk, just don’t be an idiot or an asshole.

Your go-to pick up line

Frank: I’m simultaneously proud and ashamed to say I’ve never used a “pick up line”, but “you haven’t met my dog?! You need to!” is a pretty good closer.

Doug:  Not my expertise but…girls love when you compliment their style I guess. I’ve also told a girl she looked really intimidating so I had to say something to her…and that seemed to work. (Probably wouldn’t recommend this unless you swag game is at 100.)

Matt: “I don’t want to change anything about you, except your last name.”

Brody:  “Hey, (Insert random Gucci Mayne lyric here)”

Best pickup line that has ever been used on you.

Frank: “Hi” or “Want to dance?” usually work pretty well on me.

Doug:  Nothing stands out at the moment.

Matt:  I honestly can’t think of one

Brody: “Did you know that over 12 million people are killed by sharks annually?” – Awesome Tinder Girl (scratches head)

PDA – yay or nay?

Frank: Meh. Don’t have a problem with it in the right time/place scenario, but don’t obnoxious about it if I indicate it’s not the right moment.

Doug: When I’m drunk it slips though.

Matt: Yay – just don’t get nasty.

Brody: Not into it. Well… a little bit. Okay.

Playing hard to get – in or out?

Frank: The game is only fun if we both have a good idea that’s what we’re playing. I don’t have the time or enough self loathing to keep chasing you if you just don’t seem interested.

Doug: Ehh, there is a line. Can’t play too hard. I guess if you do it right it works. There is one girl I can’t really read and it’s frustrating in the best way.

Matt: F*ck that

Brody:  I do what I feel. No real strategy to it, I just shoot from the hip.

Deal breakers?

Frank: Penises. Holocaust Deniers. Lack of sense of humor, otherwise known as ‘failure to laugh at my jokes’.

Doug: Chain smokers. Hygiene. Too much makeup. Wedges are pretty awful too, they’re not a deal breaker…but I’m just saying. (OK, you’re just wrong on this one, Doug.)

Matt: Talking excessively about an ex. Asking about my exes. Being on your phone the whole time. Getting sloppy drunk – by yourself. Being super independent – it’s the first date: I’m going to buy, I’m going to hold doors and I’m going to compliment you, just go with it.

Brody:  I call it Pirate Code. (Does any one know what Pirate Code entails??? Anyone? Anyone?? Ok.) Simple stuff you either do or don’t do that everyone knows. If the Pirate Code is violated, deal is void.

When is it acceptable to have the “what are we doing” talk?

Frank: Later than you want. We can never ever go back to the “not sure what this is yet” stage, let me enjoy its sweet, innocent, consequence-free excitement for just a bit longer.

Doug: I don’t know. When you can openly disagree without it being uncomfortable. At least you know you are past the fake sugar coated stuff at that point.

Matt:  Whenever you want. If you want it – why wait around and play stupid games? If it doesn’t go the way you wanted then you know sooner and can move on and find someone who feels the same way. If it goes well, you’ll wonder why you waited for so long.

Brody: If I’m hanging out with you, I already like you. Except for sometimes when I don’t. Does that help? (Honestly, Brody, this couldn’t possibly be less helpful).  And, if you have to have a talk about it, chances are it’s going in the wrong direction anyway.

Proper break up protocol*

Frank: Call a spade, a spade. If you’re over it, be done with it – no one likes being lied to, or having their time wasted.

Doug: Face to face. Hammered. Then re-evaluate it in the morning.

Matt:  Give me my favorite sweats and hoody back that you stole. Be civil and chill in public but fair game behind closed doors or via phone If cheating is involved– literally whatever evilness you can think of.

Brody:  Make sure she gets all of belongings back. Don’t yell. Do your best not to be a jerk.

*Not mentioned: faking a tragic situation and forcing your friend(s) to call you during said break up conversation. Probably left this out because IS NOT proper protocol. Just in case anyone, Matt, was confused. 


In review:

  • Boys think about these things more than we give them give them credit for
  • Your mom was probably right, don’t sleep with your date on the first date
  • The old fashioned rule of “boys buy” stands true, at least on date #1
  • Double texting is still dangerous territory
  • Boys don’t pick up the phone and call enough
  • Avoid f*ck bois at all cost

What else do you want to know? I’ll ask the questions and you get the answers. Leave your questions in the comments below!


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