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30 Things Every Guy Should Know About Dating By the Time He's 30

From knowing how to apologize to how to break up with her, 30 dating skills a guy needs to have down by the times he turns 30.

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Calling it swagger would deeply undercut the idea, but there are certain men who just get it. They know what to say to a woman and how to say it. They know how to touch a woman. How to make the most nonchalant among us crack a smile, even a hearty, whole-body-shaking laugh.

These aren't always the most attractive men, but one things for sure—these are men. Whether in conversation or in bed, there is a distinct difference between a man and a boy. An effortless way about him that's the product of roughly three decades of triumphs, terrible mistakes, and the knowledge that comes from both. Whether you're 21 or 35, commit to mastering these 30 things every man should know about dating by the time he's 30. Trust us, she'll notice.

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30. How to give her a truly thoughtful gift.

This all comes down to listening. She mentions something she wants. Maybe it's in passing, or maybe she's blatantly dropping hints in hopes you won't ruin another holiday. You write it down on a note in your iPhone, and three months later, when her birthday/Christmas/Valentine's Day comes around, you purchase said item. And please, wrap the damn thing. Nothing says IDGAF like handing her a box or tossing it in a random bag without tissue paper.

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29. How to feel jealous but not act on it.

Seeing someone flirt with your lover at a party should not be threatening. It should be delightfully unsettling. And, like the guy who struts in with the same double monks you bought last week, it should be infuriatingly flattering. Watch, exchange a knowing look across the room, and go back to attending to your whiskey. Later, when you're alone, whisper unsavory things about how her ass is in demand, and it's yours. Jealousy is sexual impetus, not an invitation to start a brawl with an unknowing stranger.

28. How to react to seeing her when you've spent time apart.

Were your cheeks always the perfect shade of pink? Were your lips always this soft? Make a big deal out of seeing her face after a several-day-hiatus, and you'll keep things feeling exciting forever. Or, for as long as you're hoping to.

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27. How to touch her.

Leave your repetetive Mr. Myagi moves for when you're Windexing the shower. When you touch a woman, it should be with a gentle, meandering motion. Don't burrow a hole into the small of her back. Trail your finger on her skin so you're barely touching her—much softer than a Swedish massage, but with enough pressure that she won't burst out laughing.

26. How to break up with her without being an asshole.

A grown-ass man should not break up with a woman over a text message or via any other method other than face-to-face. Be honest, but not too honest. A breakup shouldn't feel like an attack on the other person's character. It should be an honest assessment of how and why your feelings have changed, without resorting to verbally assaulting the other person by enumerating their faults. That's not honesty; that's emotional terrorism. Also, don't wait longer than neccesary to rip the band-aid off. You're not saving her feelings, you're prolonging her recovery.

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25. How and why birth control works.

It's science, bitch. If you expect her to take on the responsibilties and discomforts of taking hormones to prevent pregnancy, you should at the very least understand how contraceptives work, and how they affect her mind and body. Mostly so you can be extra-appreciative of her bearing that burden so you don't have to endure condoms. If that's not selfless, I don't know what is.

24. That shit talking your ex doesn't make a woman feel better about the relationship.

Being a gentleman is important. If you're smack-talking your ex, we'll either assume you're not one, or that you're not over her (if you were, you'd be indifferent). And of course, we'll be fully aware that if we ever part ways, you'll be talking that talk about us too. Not a good look.

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23. That he should never speak the words "You're being crazy" outside of the bedroom.

Something that sounds sexy when you're ass naked sounds like an invitation to have a screaming match when said in public. She's crazy (wink, wink) not crazy. Get it right.

22. How to buy her flowers without it being a holiday.

Flowers on her birthday (especially when not accompanied by a legitimate gift) are boring and unexceptional. But flowers on a Tuesday for no reason at all? You're so money. And by money, we mean, getting laid tonight.

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21. How to live with a woman.

There Will Be Hair. In the drain. On the floor. In the bed. Stop complaining. The key to keeping living together fun and sexy is to respect one another's privacy and personal space (yes, even if you have a 500-square-foot apartment). Other things to keep in mind: her towel is for her ass only. She has -99% interest in hearing about your bowel movements. Personal hygiene doesn't become optional when you begin co-habitating. In fact, we advise you take things up a notch. How else do you expect her to get excited to see the face when she sees every morning and night? Living together is easier in some ways, but keeping that sexual UNGHH become a lot more work. Take time apart often. Clean the apartment for no reason. And commit to having at least one official date out of the house each week. UNGHH offically brought back.

20. How to be honest about his sexual preferences and desires.

Sex should not be like playing Guess Who? If you're the sorta shy guy who really likes when women wears pencil-thin stilettos and walk on your back, tell her you're that guy. There's no shame in your kinks. Just, you know, don't tell her about them on the first date. There's a timing to this sort of stuff.

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19. How to introduce her to his family.

Set her off on the right foot. Show your family that you love and respect this woman, and they'll do the same. Make both parties feel comfortable and encourage them to be themselves.

18. How to apologize.

A man should know how to say "I'm sorry" and be heartbreakingly sincere with his words. A world of woe can be erased with the earnest admission that you were wrong. Just don't think an apology is a magic eraser you can carry around so that you can copiously fuck up. Be an ass rarely, recognize when you are, and make concessions with the appropriate amount of groveling.

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17. How to act around her family.

Be kind, but not overbearing. Don't come empty-handed.

16. How to introduce her when you're out.

If you're at a party, don't let her stand there awkwardly clutching her champagne glass like it's a life preserver. Introduce her; "This is my girlfriend, X" if you're dating exclusively, or, "This is X" if you're seeing other people/undefined. Never say "This is my friend, X." Unless you want to know how her champagne tastes...as it runs down your face.

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15. How to navigate relationships with her female friends.

Don't be that weird boyfriend that all of her friends feel uncomfortable around. Know the whisper fine line between being friendly and being flirtatious. The aim is for her friends to like you, not like you.

14. How to talk to her about her period.

Know how to talk to her about her period without resorting to weird euphemisms like "your friend" or making assumptions about how she might be feeling based off a Midol commercial you saw once. Bonus points: if you know roughly when it is.

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13. The difference between making love, having sex, and fucking.

You think you know the difference, but you probably don't. Tender and intimate, rough and unpredictable, and somewhere in between, these should all be in your sexual reproire and you should know when it's appropriate and most effective to deploy each.

12. How to make her a meal.

Some of us are naturally intuitive with a pan in hand. If you're not one of those people, thankfully, recipes exist. Don't wing it if you don't know the difference between paprika and cumin. Follow a simple recipe down to the letter. Even if your chicken is as dry as Aubrey Plaza's wit, she will appreciate that you went through the trouble to feed her, and it will be 92944284x more romantic than ordering delivery. Of course, she'd appreciate a moist chicken more. Work on it.

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11. How to sext her. (Hint: this doesn't involve dick pics)

There's an art to this sexting stuff. Don't just fire off a pic of the outline of your dick in your boxers (OK, now that blushy-face emoji is creepy). The idea is flirt and play with the idea of suggestion. When in doubt, do the opposite of what your grammar teacher advised: tell, don't show. Save the showing for when you're one-on-one, when accidentally sending mom a crotch shot is an impossibility.

10. How to take care of her when she's sick.

Almost all men need to be babied when they're sick, and—you know —that's OK. Being sick is a time to be unapologetically vulnerable. Even the toughest among us are turned into whimpering 8-year-olds wussies when we're reduced to a tender, sneezing heap of human. This is the time to play the caretaker. Be at her beck and call. Do the cliché yet always appreciated chicken soup and cold meds thing. Make her feel like you really know how to tend to her needs when she's at her weakest, and she'll see you as a pillar whether she's sick or not.

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9. How to order a wine at dinner.

Again, this is not about gender norms. It's about showing her you're capable, confident, and in control. It's sexy, yes, but it also allows her to relax. Even alpha females like taking a break from calling the shots. If you sit down to dinner, and take the reigns, err, wine list into your hands like its a book you've read many times, and confidently choose a nice wine, she will regard you with the kind of respect that is reserved for men who can do these kinds of things. Hint: there are not many.

8. How to make her feel comfortable when you go down on her .

A woman wants to know that the man between her legs really wants to be there. Don't think of going down on her as a race. There is no direct route to the finish line. In fact, staying on the proverbial path will take her to orgasm, but not the stars. Take your time so she feels like she can take her time. Get creative down there. Just don't bite. Her clitoris is not a chew toy.

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7. How to make her feel sexy as hell when she's naked.

If her clothes are off, you need to make as though lightening just struck within an inch of your foot; be awestruck, grateful to be alive, and incredulous of mother nature's handiwork. Say "wow" several times even if you've seen her naked three times that very day. If you have anything in your hand, drop it, and reach out and touch her. Don't always try to turn it into sex. Sometimes you just have to admire from a distance. And sometimes you have to carry her to the bedroom, lay her gently on the bed, and do work on that naked body. Both are integral to making her feel like heavens drop when her panties do.

6. How to listen.

No, there won't be an exam afterwards. But hell, look alive! Whether she's talking about how she's debating between dark rinse jeans and that sort of '80s faded denim or discussing the promising meeting she had with her boss, you should know how to focus on her words so that she feels you're interested in what she has to say and her feelings. This means asking a question or two to dig deeper and occasionally making small comments, like, "Wow" and "That's crazy."

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5. How to spend time apart without being jealous or awkward about it.

Occasionally, even if her laugh sounds like tiny bells being rung by angels, you'll want to take some time to yourself. And, she'll almost certainly want to do the same. When you're each out doing your Mr./Miss. Independent thing (which, by the way, should be often) you should know how to give her the distance to explore her interests outside of you without giving her a guilt trip (yes, that includes whiney text messages and passive agressive tweets). In fact, you should encourage her to pursue her passions and do things that have exactly 0% to do with you. The distance will be good for you both.

4. How to surreptitiously pay the check thus avoiding an awkward moment.

No woman expects you to pay the check every time. But if you pull this move on a first day or a special occasion, it's undeniably smooth. When she gets up to go to the bathroom, hand your waiter the credit card and ask him to return as promptly as possible. Quickly sign the check. When the time comes to leave and/or she inquires about the check, casually say, "I've taken care of it." Stunt 101.

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3. How to ask her on a date.

Many a man's stammering and inability to get to the point has ruined what could be her first memory of just how slick you are. Get this right. It's a first impression thing. Act at least 25% more sure than you are that she will say yes. Tell her you would like to take her out, and that you have a plan. Ask her at least a week in advance. Don't make her make the move or ask for clarification. It's not about chivlary, or gender expectations or any -isms. It's about showing her you're the type of guy that gets things done. Even if you're not, that initial impression will last 3-6 months, and by then she'lll be stuck with you. Good job, sir.

2. How to give her a sincere compliment.

Maybe you're one of those guys that compliments your S.O. all the time-stop it, now. Compliments are only effective if they're sincere and slightly unexpected. If she'd decked to the nines for a wedding and pulled all the stops (shout out to those red-bottom stilettos), she expects you to tell her she looks good, amazing even. But if her eyes are half-open (OK, crusted half shut with eye gook and yesterday's mascara) and she hasn't brushed her teeth and you tell her you've never met anyone more beautiful her heart will race a little bit. It might even make her vagina twitch. Next stop-morning sex. You sly fox, you.

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1. How to be loyal.

I'm not going to tell you not to cheat, because I'm not your life coach. Your take on fidelity, flawed or otherwise, is your own. But at some point, you'll want to be a man of honor. A man whose word means something. It may be a decision you make for personal reasons, or because you meet a woman who's courage and kindness you deeply respect. When that happens, you'll decide not only want to show others respect, but be respectable. Being just and kind and honest demands that, mostly because a man who acts this way respects himself, and demands that others treat him the same.

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