A Step-By-Step Guide (for Adolescent Boys) to Getting (and Nailing) Your First Kiss

Teenage boy with braces smiling near girl reading.

So you woke up today and decided you should probably get the whole “first kiss” thing out of the way. There’s a ton of pressure around something that seems really unimportant, and the fact that this is all your social group cares about recently is annoying. Why can’t we just play video games and eat Eggos like before?

If this is your mentality, all of your friends have probably hit puberty, and you’re what we call a late bloomer. This is fine, because if you haven’t started growing taller or getting body hair and a deeper voice by the time you’re in 9th grade, science shows there’s only a 1-in-3 chance you’ll stay like this forever.

However, I highly recommend waiting until you actually want your first kiss. This will make it way more satisfying for you — and for the lucky lips you end up smooching — but we’ll get to that later.

Let’s hit reset

Today, you again woke up underneath what looks to be a goddamn circus tent in your bedsheets, and the first thing you thought about was naked girls. (Or boys — this advice becomes largely universal with just a few substitutions of language.)

Your hormones are a fucking mess. Your face is a whack-a-mole game of pimple popping, and the slightest emotional or physical stress puts 10-inch puddles of sweat under each armpit. On top of this, it’s impossible to focus on anything scholastic now that thongs are starting to peek over waistbands like the first unexpected sunrises of an arctic spring.

Kissing a girl — and not that wiry hair growing around your knees and ankles — marks the first step in a long journey toward manhood. By manhood, I mean a committed relationship with a woman you love and sharing a bed with her on a regular basis in which she’s made you terrified of both farting and snoring.

What I’m proposing isn’t the fastest way to grab a first kiss, but it’s a better way. And as much as it pains me to do so, I will teach you how to be a competent, respectful, romantic, and tender makeout companion.

Who needs this advice?

Before we get into it any further, let me say: this post is for adolescent boys/men who want to be gentlemanly and sophisticated lovers (in the future). Two types of people don’t meet this criteria.

One, you’re not an adolescent. The WHO defines this range as 10-19 years old, so if you’re in your 20s or 30s and haven’t kissed anyone yet, you may have to pick and choose what to take away from this article. That is to say, it all still applies, but it’s imperative you don’t tell your first kissing partner it was your first kiss. She/he might be able to tell, but you can never admit this. You’ll probably have to think of some fake past in which you’ve kissed many people, but you were always drunk or something, so no relationships caught-on. Or perhaps you fell off a bicycle when you were 14 and woke up from the coma last week.

Two, you have no ambitions of being a kind, confident, and unthreatening figure towards women. If this is you, please change. The amazing thing, which you may realize someday, is the objects of your sexual desire are people  — real people — just like you! They have interests, feelings, fears, ambitions, histories, and personalities (again) just like you. The best way to date, build relationships with, make love to, and kiss them is to acknowledge their personhood and rationality. You can do this through meaningful conversations and signs of respect, which we will get into later.

Finding the right kissing partner

The person with whom you choose to share your first kiss should be someone you like. Notice, I didn’t say love, but you should like them in a crushworthy way. The reason being, should you succeed, you’ll have fond memories of the moment. If you kiss just somebody, it won’t feel like a real first kiss. You’ll forever remember your first kiss as the one you had with the person you cared about, not the actual first one, and then you’ll always have to include an asterisk in your romantic history. (First kiss stories are usually hilarious and entertaining fodder for grown-up conversations).

Also, the person you kiss should like you too. If one person is really feeling it but the other is just so-so on the whole thing, you can definitely tell. It takes four eager lips to truly sense the magnetism at work.

And I’m not saying this is going to happen, but timid young men are prone to relationships. That is to say, maybe you just wanted to dip your gangly teenage feet into the waters of romance. A kiss is just a kiss, right? Well, I’m here to tell you that physical affection is a powerful drink when served up fresh. One kiss might become two, which might become a girlfriend.

It’s very, very possible your kissing partner wants something similar to you, whatever that may be. Homework, track practice, band, and hanging out with your friends are huge commitments that both adolescent girls and boys stress over. If padding your college applications with extra-curricular activities is important, you simply don’t have time or energy for hanky-panky.

But… you should be prepared for the possibility that this kiss could lead to something more, and if it does, you cannot be embarrassed or regretful of that outcome. Ten-bucks says if your friends make fun of you, they’re actually extremely jealous.

Step 1 – Find a place

Find a place that’s out of the public eye (i.e. not around your friends or peers). This place should be one where she feels safe, but also private enough to let sparks fly.

It’s scary and hard to do such vulnerable things — especially in high school — but if you can manage to disassociate yourself from your physical and spiritual being for a brief moment, asking her on some kind of “date” or “exclusive hang-out” is a real big-dick move. Nobody expects that kind of confidence from a dweeb like you (least of all you), but doing hard things sometimes has big rewards. And if she says no, just be like, “Yeah, that’s totally cool,” then literally run away.

Step 2 – Find a time

The right place comes before the right time because you’re gonna want to give yourself a long, long runway for actually pulling the trigger. Find a place where you could feasibly kiss before having your most well-concealed anxiety attack ever.

Beyond that, if you’ve been talking naturally and making each other laugh, the green light is there — you just need to put your foot on the gas.

Look for other signs of flirting. Lots of hair touching, mirrored body language, lip biting, etc. If she seems just as nervous as you as a potential moment approaches, that’s a good sign.

Step 3 – The move

In a perfect world, you’d have started making it clear early on that you’re interested in being physically close. Hand holding, “playful” touching, and the too-occasional-to-be-coincidental bump while sitting and walking are all good signs.

However, you and I both know this feels painfully awkward and maybe a little creepy. The moments directly preceding the kiss will probably be your first indications of actual physical intimacy. You’ve got two options, bro.

  1. Wait for a natural pause in conversation then go for it, kind of slowly. Speed matters, because if she doesn’t want to do it, she’ll have time to pull away. If she accepts, proceed to Step 4, if she rejects, say something like, “Ah, my bad, you look pretty and I thought it would be fun.” Then (the fuck if I know), melt where you stand?
  2. Say you’d like to kiss her and ask her if it’s okay. Verbal confirmation, while maybe awkward, is a clear indicator of permission to approach Step 4. If she says no, feel free to melt a little less than you would if you went with option 1.

Step 4 – The kiss

Let me be extremely clear: I don’t want to write this section. It feels a bit like describing how exactly I fold toilet paper. Just too intimate in a very cringeworthy way.

Alas, the internet needs content.

Close your eyes just before contact is made. Your lips should be slightly extended, but not puckered like a cartoon character. Think soft, but intentional in movement. Lock on to one of her lips (probably the bottom one at first) and linger for a moment (2-4) seconds. Unlock your lips, linger another 2–3 seconds, and repeat the first lock. This whole process takes about 10 seconds.

After this, pull back a few inches and wait. Take your cues from her. If she pulls away, you pull away. If she stays for more, you go for more. If she goes for a different lip lock from the first one, you go with it too.

At some point you’ll need to use a bit of intuition. This is what separates good kissers from bad ones. Find a rhythm that feels right for the moment. Tender = slow, soft. Impassioned = fast, firm.

I should really stop here. Once you get that first kiss, the rest is the wild west and unique to each situation. My promise has been fulfilled. But a few more pointers can’t hurt.

Step 5 – What do I do with my hands?

It’s your first kiss ever, so don’t be an idiot. Place your hands gently on an area of her body that feels personal but wouldn’t get you suspended from school. Waist? Lower back? Nape of the neck? Keep them there throughout the kiss. If she’s really feeling it, she’ll put your hands where she wants. Overswinging usually leads to a slice (golf reference), and it’s important to give yourself a decent second shot, even if it’s just off the fairway.

Step 6 – What about tongue?

If a kiss lasts longer than 30-seconds, tongue may be acceptable. If this is the case, introduce your wet oyster innards in phases. You’re not trying to dig the last bit of peanut butter from the jar. Start with one swipe, then two. Never more than three at a time before returning to normal-person kissing.

And if you kiss with tongue, try to make it soft, like your lips. No one wants to feel like an alien-worm is invading their oral cavity. I mean, some people might, but I’ve not met them.

What now?

If you’ve managed to snag your first kiss, please stop before your lips are chapped.

And honestly? Hang out as long as it still feels natural, then go home. Maybe kiss again before you say goodbye.

You (probably) have a long life ahead of you, which leaves plenty of time for other romantic experiences. Dwell on what you liked and didn’t like about your experience and remember to be patient.

Lastly, first kisses are great, but having a reliable kissing partner is even better. Growing with another person in a physical and emotional capacity is almost as good as YouTube or Instagram scrolling in terms of addictive fun.

How can you maintain contact with this individual in a way that’s not creepy and preserves your sense of coolness? The secret is to treat them like you would anyone else you care about. Shocking, I know, but responding to texts, listening to their desires, and (importantly) communicating your own hopes and anxieties creates an honest relationship.

I know, that’s not what this blog is about, but when you’re a 30-year-old man giving advice to basically-children about kissing and romance, it’s hard to refrain from dumping every bit of stored knowledge at once.

Okay, last time. Talk to girls (or boys). Remember they’re cool individuals, just like you. Remember to be respectful and considerate of their desires. Don’t go for tongue immediately.


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