Title: Lessons Learned Along the Way (or, Four Girls and One Guy Shikamaru Dated Before He Found His Soulmate)
Author: Jakia
Word Count: 2,017
Summary: Growing up is troublesome: dating is troublesome. Doesn't mean you don't learn something about yourself with each person your with. [Shikamaru/Ino, Shikamaru/Sakura, Shikamaru/Shiho, Shikamaru/Naruto, Shikamaru/Tenten, and endgame Shikamaru/Temari]
A/N: I hate it when I read fics where sixteen or eighteen year old Sakura has her first kiss with her one-true-love Sasuke, an then they get married and have a crapload of babies. Oh please. These are teenagers, and ninja. The Rookie Nine has probably been dating each other for years, especially since Naruto was off training with ero-sennin. So I thought to myself, wait I ship Shikamaru with Temari, they're my OTP, does this mean Shikamaru has dated other girls before Temari? And my subconscious was all like, yes, Write It. So I did. Hope you enjoy it as much I did.

Lessons Learned Along the Way


He is twelve. He is twelve, and he is still more of a boy than a man, and this is his first relationship with the opposite gender.

He asks her out because Ino is sad now that Sasuke has left, and Chouji is still too injured to move much. He can even admit that Ino is pretty, which is saying something for a boy who has just barely realized that girls don't have cooties.

They last less than a week. It's too…awkward. In later years, Shikamaru will be able to pinpoint the problem as the fact that they both see the other as a sibling, and they feel little-to-no attraction towards the other.

Still, the week is an informative one. He learns things about himself that will affect him later in life, things that let him know about his own tastes in women.

Like the fact that he likes blondes. He doesn't know why, but yellow colored hair calls out to him like water to a man dying of thirst in a desert.

Or that he prefers girls with a little more heft to them. Holding Ino is like holding a bag of bones and just as comfortable. Being with Ino allows him to appreciate the fact that other girls have curves--they are "fat" perhaps, but in all the right places.

The most important thing Ino teaches him, however, is that woman are not always troublesome, provided you can get them to shut up first.


Ino sets them up. Shikamaru is at the point where he would rather die than actually date the Sasuke-obsessed Pink Wonder, his week-long relationship with Ino six months ago being his quota for female contact for the year. Still, Ino is trying, so he figures he might as well show up.

As it turns out, Sakura is a lot more fun when she's not screaming Sasuke-kun in your ear. They manage to date for about three months given the fact that they are both fairly intelligent people who can have a good conversation and still enjoy the kissing.

It's only when he takes her out for ramen does he realize it's not going to work. He should have known---stupid!—not to take her there, that there would be too many memories in that place, but for once his genius fails and he's stuck on a date with a girl crying into a bowl of ramen.

They break up shortly after, on purely amiable terms. It's hard to date a girl who is already madly in love, and Sakura understands that. They're still friends. He still misses the kissing, though, even if he will deny it above everything else.

Being with Sakura teaches him something, though: he needs a girl who is smart. Maybe not as smart as he is, but smart enough to have a deep conversation and keep it interesting.

Basically, he needs a girl who is good at shougi, and he finds he's okay with that prospect.


After Sakura, it's a full year before he has any romantic intentions towards any female. Shiho is everything he thinks he would want in a woman: she's smart, blonde, not too pretty, not ugly, not a stick, and best of all not troublesome.

She's a ninja, yes, but she's so low ranking that he would never have to worry about her being in any danger. Her glasses are a little crazy but endearing after a while. She is smart, yes--she wouldn't be in code-breaking if she wasn't. She is a wonderful cook and she is so sweet she wouldn't hurt a fly. They never fight, they never argue, they never disagree on anything. His word is final and of course he's right about everything.

It's perfect.

It's boring as hell.

She's good at shougi but offers no real challenge. They have no friends in common--his friends think she's weird and he thinks her friends are weird. And she's so damn quiet that half the time when they are out in public he forgets she's even there.

He dates her for a long time. Longer than he's dated anyone else in his life. Still, after six months he has to admit to himself that she isn't The One. She never will be. He isn't even sure he's attracted to her anymore. Kissing isn't fun like it used to be.

So he breaks her heart and she cries and cries and cries. He feels like the biggest asshole in the world but doesn't regret it.

Shiho taught him one thing and one thing only, and it's been the toughest thing for him to swallow: he needs someone troublesome. He needs someone to argue with; he needs someone to look him straight in the eye and tell him he's wrong. He needs someone to motivate his sorry ass; he needs someone who will fight back.

In other words, he needs someone who will stand at his side as his equal, not someone who will stand behind him in his shadow.


He is single and she is single and Tenten is hot. That is the only explanation anyone can give as to why they get together, and they aren't far from the truth. As it is, Tenten really digs the dark-haired genius type ("I thought I'd try dating one who didn't have a stick up his ass.") and Tenten is fairly troublesome, what with her temper and the violence and the love of weapons and all.

It's Tenten who teaches him how to make-out, really make out, tongue and lips and teeth and the whole troublesome experience. It's Tenten who teaches him how to touch a girl, how to make her moan, and how to give a proper hickey, one that a girl can't hide that well that will make her friends green with envy. It's with Tenten that he learns about kinks—blood and bondage, knives and shadows, using his family techniques for things that leave him with chakra exhaustion but completely and utterly satisfied.

He doesn't sleep with her but finds himself wishing he had, hours after she's left for the night. Tenten is his first object of lust that he can touch, the only girl he's been able to fantasize about at night and then wake up in the morning and act on such fantasies. They don't talk much but Shikamaru doesn't mind. For once the lazy genius finds something that lights a fire up in his gut---if just touching feels so good he can only imagine what sex is like.

A few months later, Tenten dumps him for Neji-Fucking-Hyuuga, and Shikamaru finds himself nursing a broken heart for the first time. He wasn't in love with her but he did like her, a lot, so it stings that she would leave him for such a pretty boy. He gets over it once he realizes how much Tenten loves Neji—genuinely loves him, and so he finds himself wishing them the best despite his own heartache.

If Tenten teaches him anything besides how to please a woman, it is that violent women were all around better, if only for the physical aspect of a relationship.


It is a cruel and senseless prank, one that Shikamaru should have known better than to fall for. Should have known that when a cute blonde in pig-tails walks up to you and asks you if you'd like to join her for some ramen---well, Shikamaru didn't think too much about it. If he had, he would have realized it was Naruto. But at the time Shikamaru is bored and hungry and the girl was cute, so he figures he should indulge his curiosity and buy the girl some ramen.

He doesn't know why kissed her later. He was just walking with her as she thanked him for dinner and it seemed like such a date-ish thing to do, to walk a girl to her apartment after buying her dinner and kissing her. So he does.

Only he realizes that kissing this girl is different than most girls. Her lips are rougher and cracked and she smells like a man. He doesn't really like it, so he pulls away and finds himself staring into the mischievous blue eyes of one Naruto Uzumaki, who spends the next three days teasing him about trying to get fresh on the first date.

If his one and only date with Naruto teaches him anything (besides do not date strangers, no matter how cute they are, and for God's sake don't kiss them that's blackmail!), it was that he was straight. Not that he ever thought he was anything else. But still. Confirmation was nice. Made him feel sure that he wasn't missing anything on the other side, whatever that was.


It's been a while. He hasn't seen her since before Pain destroyed the village, and then Danzo became Hokage, so relationships between the two villages have become estranged. The ties between the two are good again, but he's a Jounin now, a pretty busy guy, with Genin-brats to teach and suicidal missions to run. She's still the ambassador though, so maybe some other lucky Chuunin gets to escort her around, or maybe she doesn't even have a guide now. He hasn't been in Konoha long enough to find out.

Still, when he is given an A-ranked mission of backing up a Suna-nin, he is not surprised to find himself fighting side-by-side with her once more. This time it's his turn to save her, though, and he makes a point to mention that, earning himself half a smile and a whack on the shoulder with a heavy-iron fan.

The battle is difficult and leaves them exhausted. He has to carry her to Konoha on his back, and rejoices in the feeling of her curves against him. Along the way, he notes that this is the sixth time he's rescued her and feels a surge of manly pride, but doesn't say anything. That can wait, he figures.

If he were honest with himself, he would admit that Temari was his perfect woman. She's angry and violent and troublesome, sexy and smart and—though she'd never admit it---kind. He knows all-too-well the feeling he gets in his gut when he sees her, knows why he can hardly breathe when she walks by. The fact that her new outfit is shorter than the last (short enough that he can fully see and appreciate the length of her legs,) and is going to cause him several sleepless nights---well, he knows that too.

They're already friends: asking her out shouldn't be this troublesome.

Yet, as he waits outside the room while she receives her medical treatment, he realizes that he's never asked a girl out before---the girls have always come to him, and he's just gone with it. This is the first time he's really taken an initiative, and the thought scares him just a bit. It feels a bit like effort, and Shikamaru has never really been that fond of effort. But the thought of not asking her hurts more than words can say, so he swallows his pride and bucks up and act like a man, for once in your life!

They leave the medical center before he gets the courage to ask her, zigzagging through the crowded streets of Konoha, keeping close as to not lose one another.

"Hey," he whispers, and his palms feel sweaty so he stuffs them in his pocket nervously. "Do you wanna, I dunno, go do something later?"

She snorts at him. "What, like a date?"

Breathe. "Yeah, like a date."

She stops in the middle of the crowded street, forcing Shikamaru to stop with her arm. She stares at him, uncertainty written across her face as she blinks, once, twice, and Shikamaru wills his heart to stop pounding so loudly, so troublesome.

She breathes, and his stomach drops. "Okay."

He locks his hand with hers, and never looks back.


A/N: Thanks Jade for being like the greatest beta-reader ever!