10 Dating Mistakes Guys Make — and How to Avoid Them

Guys do some really dumb stuff, particularly when around a woman they like. Making too many stupid mistakes while still in the courting process can end a relationship before it had time to get off the ground. And that happens all too often in today’s world.

Here are 10 dumb dating mistakes guys make and (despite their ineptitude being in the best interest of guys with a little common sense) how to avoid them.

Show up without a gameplan
While you should never have a rigid plan for much of anything in life, you should at least have a concept of how you want your date to go. Have a loose plan for what you’ll be doing and where you’ll be going on the date, and it’ll show that you’re capable of making decent decisions as well.
How to Avoid It: Ask yourself before you leave for the date “If everything goes perfect, what will we do on the date? Where will we eat? What will we do after? Etc.” Then go over the answers to the questions on your way there, so you can say them semi-assertively when the moment arises.

Forget (or not listen to) what you know about her
How annoying is it to be asked the same question multiple times? It’s pretty frickin’ terrible. Don’t be that guy, and keep in mind all of the hints she’s dropped already about her likes and dislikes. Women are way better at subtle hints than guys are, so think of it like a game of Clue.
How to Avoid It: Pick out a handful of important things to remember about her and use whatever methods used to work for you on high school tests to keep them fresh in your head before a date.

Say things directly opposing their best interests
This one's for those guys who say, “I’m not looking for anything serious,” and then immediately catch feelings. Or “Maybe we should just be friends” mere minutes before they hook up. If you know you’re looking for one thing, you don’t have to be blunt about it but don’t outright deny it. Maybe she wants what you want but you keep telling her it’s not what you’re looking for.
How to Avoid It: Be honest with yourself about what you want so you can be honest with her.

Bring a terrible wingman
Shoutout to the dudes who bring their married/boring/unattractive friend to “entertain” a woman's friends while he tries to get lucky with the isolated target. If your wingman isn’t at least good enough to hold the friend’s attention, how is he supposed to give you a shot with the one you’re interested in?
How to Avoid It: Get a wingwoman (really), or fly solo, or at least use a wingman who knows what he’s doing.

Lack confidence
Too much confidence can also be a killer, but coming up short on it is a lot more common. Confidence can be faked as well as anything, so there’s really no reason not to pretend to be at least remotely cool with yourself no matter how self-deprecating you really are.
How to Avoid It: Whenever you start to get nervous around a date (or potential date), think of a song that makes you feel like you’re the greatest, even if it’s “All Star” by Smash Mouth.

Not offer to be a gentleman
You don’t always have to pay for a lady’s meal, but it’s polite to at least ask for the first few times. Same thing with holding doors and table manners. Plenty of women will decline the kind gestures, but the thought alone is worth more bonus points than you can count.
How to Avoid It: Hold doors open, offer to pay for her meal, suggest other little things you can do to make her life better that she’ll probably turn down.

Act outright mean
Yeah yeah yeah, women dig assholes or whatever. Being a little snarky can sometimes work in your favor in the dating world, but there’s a line crossed all too often these days. Don’t be mean just to be mean; nobody likes that.
How to Avoid It: Make sure that every “mean” comment you say is at least as funny as it is mean. People like funny.

Expect sex on every date
Sure, sometimes you go out and end up getting some. Great for you, that’s really cool. Sometimes you don’t, and you have to realize that it’s totally fine. When you stop trying to stick it in every woman you’re mildly interested in, you’ll realize how much easier life is when not driven by constant expectations and desires for sex.
How to Avoid It: Go into a first date (and often a second/third date) assuming you’re not going to get laid. Be prepared, just in case you do, but then at least it’ll be a pleasant surprise if it does happen.

Use terrible pickup lines
Seriously, guys out there say things like, “If you were a fruit, you’d be a fineapple.” And yes, quoting Fetty Wap does count as a terrible pickup line. Thanks for making opening conversations so much easier for the rest of us, fellas.
How to Avoid It: Use something simple like “Hey, I like your shoes.” Even if it doesn’t work, you’ll feel less dumb.

Text something totally inappropriate
There’s a time and a place (and a recipient) for every text. If someone tells you their grandma died, maybe don’t text them the next day telling them that they’re hot. If a woman you’re dating might be a feminist (probably a good thing to assume), don’t send her the misogynistic joke your old frat buddy sent you. We’re hoping everyone is capable of reading situations in person well enough to not shoot themselves in the foot so blatantly, but the stupidity of dudes should never be underestimated.
How to Avoid It: Before you text someone you want to sleep with something, ask yourself if you would say that to them in person when they’re in a bad mood. That’s the answer to whether or not you should send it.
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Josh Chesler
Contact: Josh Chesler