•It honestly depends on how much younger they are. When we’re talking ‘younger’ I imagine much much younger as opposed to just a little 3 or 4 year difference. In which case, Shikamaru might consider it a drag under certain conditions

•If they’re naive, that’s a definite problem. Shikamaru has a particular disfavor for naivety, in case that’s not obvious. He might get a little annoyed, but forces himself to overlook it because hey, he really likes them. It’s a flaw he’ll deal with. He might even talk some sense into them? Help them work toward maturity? 

•He makes so many jokes about it though. Of course, as long as they’re okay with that and don’t take offense to it. He’ll call them kid, tell them it’s past their bedtime, ask them if they need to be escorted to their academy classes in the morning—all random little things. You know Shikamaru got the jokes

•Now those are all just fun and games, and might occur during the “friendship” stage. Where Shikamaru knows he likes them, but doesn’t know how they feel in return. Shikamaru is not one to put pressure on them. He can patiently await any signs that might point to the reciprocation of his feelings. Although, Shikamaru is also the guy whose relationship would just kind of… happen. They’d probably kiss randomly at some point and there you go, they’re a couple

•There is one point where he asks them if they really want to go through with this. They’re younger, he’s older, he doesn’t want them to face any repercussions because of that. I have a suspicion that there weren’t many scornful looks for relationships that had a wide age gap in the Naruto verse, tbh. But Shikamaru thinks it’s better to be safe than sorry. He’s not an insecure, doubtful guy by nature, but when it comes to this relationship, he might be. He just needs to make sure his s/o knows what they’re getting themselves into

•He’ll probably make even more jokes about it, like “Just know when you hit the pinnacle of age in your thirties, I’ll be getting old and wrinkly. As long as you like me when I’m old and wrinkly, I think we can make it work. Even if you don’t, just make me believe that you do. Ignorance is bliss” I just imagine him saying this while he’s sprawled out on the couch with a book over his face or something tbh

•One thing I want to put out there though (and this may be sappy for Shikamaru idk) but age doesn’t really matter to him. He’s the type who could marry someone ten years older than him and he’d be happy. As long as he loves them for who they are, and vice versa, that’s all that matters. Once love takes form for Shikamaru, there are very little materialistic factors that can change that