How To Win At Dating


So. You’re single. You’ve won the break-up. Now what?

Well, my darlings…

Now we date.

Confession? I like dating. If it’s fun, I have a good night. If it’s terrible, I have a good story.

I’m pretty good at dating, so I’d figure I’d share how I try to do it. Without further ado, How To Win At Dating, with more very staged pictures of me after the jump. (I mean, I have lipstick on and everything)


(Step zero: Practice your “I’m attractive no really this is not just the make up and the dress and great lighting oh and also I am so interested in what you have to say” demeanour)


Choose who you want to date wisely. Not because you’re a delicate little flower protecting her virtue, not because you decrease in value based on the number of guys you fucked dated, but because there is NO use spending any amount of time with anyone you’re only tolerating.

Not in romance, not in friendship, not ever.

As written in this article, I don’t like wasting my time. So I’m selective in who I want to spend time with.

You know that wardrobe trick that if you don’t LOVE an item when you’re wearing it in the dressing room, you shouldn’t buy it?

Yeah. That same principle applies to dating.

If you’re not feeling someone’s dating profile, if the first impression is only so-so, if the first date is average at best?

You’re not going to love him spread-eagle tied to the bed covered in marinara sauce.

Not even when it’s the good homemade kind. Not worth it.



What are you trying to get out your dating experience?

Fun? Sex? Quick fling? A relationship? An antidote against your own crippling insecurities*, loneliness and/or fear of death?

I’m not saying that you will get that. You’re dealing with other people, with their own wants and needs, that might not be compatible with yours.

Additionally, you might find that your desires change as you go undergo new experiences and meet new people.

But it is good to give it some thought.


See, sometimes things go your way, and that stud muffin you have your eye on turns out not to be a serial killer. Or that fling was exactly what you needed. Or that girl falls head over heels in love with you too.

And other times you go on 101 terrible first dates, you end up struggling your way through a huge mismatched blind date or the guy who seemed great at first turns out to be a huge dickwad.

Who knows what will happen.

Point is, don’t put all your hopes and dreams on this poor unsuspecting person you’re spending time with, don’t expect too much of strangers.

And for God’s sake, don’t order your wedding dress after you get a Tinder Match Notification. That shit is usually non-refundable.



So let’s say you found someone you wouldn’t mind living through the Hunger Games with, and you want to go spend time with them. Great.

My personal recommendation for the first date or even the first few dates? Go do something where you can actually talk.

I know going to the movies is a popular first date thing, but you can’t get to know someone if you’re in the movie theatre, silently watching the same movie. And if they talk a lot during the movie you might have to punch them and that’s not cool either.

Go out for drinks. Drinks are perfect. You can really talk to each other.

And you know, drink. 

(Coffee dates, active dates and dinner dates also work well)



Do you want to go on good dates? Be the type of person you would want to be on a date with.

Be a decent human being to the other human being!

Be warm, kind and interested. Ask questions, help them win that game at the fair, hold their hand if they’re scared during the movie, share your dessert (even especially if it’s so good you kind of don’t want to).

If you are having a good time, tell them.

If you think they’re good looking, funny or sweet, tell them!

If you like someone, tell them (without adding a marriage proposal straight away, ya loon).

Disclaimer: None of this applies if the person you’re on a date with is a total asshole. Then (if stopping the date as soon as you figure this out isn’t an option) you can be as uninterested and unpleasant as you like.



When you’re dating, it’s important to be able to accurately assess the way things are going. So try to always look objectively at the other person’s behaviour.

If they tell you they like you, okay. If you have a few dates and suddenly they vanish into thin air and you don’t hear from them again, okay (BYE!). If they seem only mildly interested in seeing you, okay. Things are what they are.

Don’t jump to conclusions about the way they are or how they feel about you. Let time tell.

Problem is that if you start to like another person more and more, you want them to like you back more and more too. This is only natural, but it really screws up your judgment. A classic mistake people make in this scenario is construing long winded explanations on why the signs are mixed or negative.

Mixed signals? Usually just one sign: They don’t like you as much as you want them to.

You ignore the fact he doesn’t talk to you for 3 days until it’s Saturday night and he’s drunk and wants to have sex. When she’s with other people she completely ignores you, but you forgive her for that because you don’t want to admit to yourself she likes you less than you like her.

While in fact, the world doesn’t end if someone you’ve only just met isn’t that into you. Your ego shouldn’t be so easily crushed. It should be okay. Don’t grasp at straws.

I mean, one of my dates moved to Yemen and another went to the Secret Moon (“Smoon”) for an intergalactic space mission and I was fine with that.


(Pro tip: Don’t be this person on a date) 


Of course you can be bummed if someone doesn’t text you as much as you want them to. Or if someone is not interested enough in a second date to ask you out again. It sucks when things don’t go the way you hoped.

But for FUCK’S SAKE.  Is it really necessary to get all cranky and depressed over it? Are you really going to let what some dude/chick does affect you that much?

I believe in personal power, and not giving it away to someone else. Especially not to someone who you don’t know that well yet anyway.

Hopefully you have plenty of other things to do or think about. Accept, move on.



As said, I’m all for being open-minded, relaxed and not letting others get to you. No need to create drama over tiny things.

HOWEVER. You don’t have to just take everything for the sake of being the ‘cool girl’, the ‘chill girl’.

You don’t need to have chill. In fact, have ZERO chill if that means you speak up for what you like and don’t like.

In this article, the author makes an excellent case against being chill and how sometimes dating can seem like a competition of who can care the least. Now that is NOT what dating should be about.

You can care, and if someone does shit you don’t like, you don’t need to have ANY chill and you don’t need to keep seeing them.



Sometimes things don’t work out. You two are not a match, she wants weird stuff in the bedroom (but like, SUPER WEIRD STUFF), your cat hates him.

This is the part where you go “Sorry [insert name here], it was fun but I don’t think this is gonna work, because [reason, but put in a nice way]. Best of luck in your future endeavours.”

When this is said to you, you go “oh okay (optional: too bad/what a fucking relief)” and you move on with your life.

(What to do when they’re giving you a dumbass cliche type of line? You STILL say “oh okay” and you move on with your life. Who the fuck cares. We’re not here to make other people honest. They are or they aren’t.)

For girls, breaking it off can be a little trickier. Experience has taught a lot of us that men can get mean. Sometimes just in a passive aggressive “fine, I was done with you anyway” way, other times in a “you fucking whore I know where you live and I’m leaking your nudes” type way.

Obviously my tip is not to get involved with the last type of person in the first place. But shit happens and people aren’t always what they seem. Be careful but very, very clear. Involve other people and authorities if you are worried for your safety.


(Step something: Fix your cleavage and hope it is moderately enticing)


Have fun.


Okay, GREAT.

Now that THAT’s out of the way I can change back into my jeans and my Beyonce shirt.

Actually, that’s another final tip: You don’t HAVE TO go all little-black-dress-and-lipstick. You can if you want to, but if you feel way more comfortable in t-shirt and jeans, you do you and wear that on your dates. The person has to like you, for you.

This was dating advice with the Self Help Hipster: It’s been real. 

In case you were wondering what is going on in my dating life, that’s very simple: I’m actually dating someone. We’re together.

I met him on Tinder a little while ago. He made me laugh so hard I almost spit out my morning coffee, I hit (on) him with a fun octopus fact** and here we are.

Life is weird.

Ok bye.

*Go see a shrink before you take out your shit on someone else, darling.

**Risky move but it paid off. 

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  1. Absolutely true! Love yourself and someone bill love you. I am dating to and sometimes it sucks sometimes it’s good. But I am happy either way! (Until this morning, broke my toe but no one to bring me to the hospital at 6 in the morning

  2. Okay, I need to send you a dry cleaning bill… I just spit out my coffee on the couch, after reading your sentence about ordering a wedding dress after a tinder match notification.

  3. This is great! I’ve been going through some ridiculous dating experiences recently, and my friends suggested I write a post (or a few) about them. Yours is so great, though, I don’t know if mine could even be half as good! Thanks for sharing these tips. They’re right on the nose!

  4. This is great! I’ve been going through some ridiculous dating experiences recently, and my friends suggested I write a post (or a few) about them. Yours is so great, though, I don’t know if mine could even be half as good! Thanks for sharing these tips. They’re right on the nose!

  5. Great article! Especially the text of step 6.. Just what I needed to read after a disappointing dating experience, thanks!

  6. Thanks for this, after a break up almost two months ago, I don’t know where or how to start again. I seriously though Tinder was just for one night stands. I’ll give it a go, though I really hate dating with a passion. :/ Thanks for the tips!