Disclaimer: I do not own the Simpsons or it's characters.

Chapter 13, Shipping: Wilmore

There are times when Seymour and Willie are complete polar opposites. They fight, scream and argue and yet they believe and trust in each other. No it's not one of the more traditional pairings, but I think they could make each other happy. Like Jimsa, I am going to name several episodes from seasons 1-5 and name why I think these two could work as a couple.

1. [Principal Charming]

Ok, this is the very first episode that has Willie in it. It is also the episode where Skinner dates Patty, so we get to see his romantic side. Alright, first of all we see Homer doing pros and cons of different people to see who would be a nice match for Selma. For Principal Skinner, his pros are: uses big words, dislikes the boy, and well-groomed. Where as the cons are: possible 'Homer Sexual'.

During the dinner, Patty is acting like her normal self, talking a trip that she hated, and Skinner swoons like it's poetry. I know that Willie and Skinner fight in the future, but if Skinner becomes physically attracted to Willie then he may act just like this around Willie. Speaking of which, Willie seems to enjoy watching Bart while he resods the field. This shows a dislike for Bart that Willie and Skinner could have bonded over.

Also, now that I think about it, if you give Patty a Scottish accent, then she and Willie would sound very similar. If Skinner finds Patty's voice attractive then he could find Willie's voice attractive.

While watching the movie, Skinner tries to copy 'The Move' from a teenager. To me this suggests that he hasn't been on a date in a while, or (less likely) this is his first date. 'First date? Really, QueenAlicorn? Seriously?' Just hear me out. When he was younger, Skinner was a lot like Jimbo, and those guys could get around, but they didn't necessarily date. Then he joined the army and sent overseas, where you're not allowed to get physical (even with your spouse). Then finally he moves to Springfield to live with Agnes who doesn't approve of Skinner dating. Also when Skinner wants a kiss from Patty he says that he 'doesnt have cooties'. Geez my high school boyfriend never mentioned cooties.

Of course all that aside, I do kind of like the innocent of Seymour's attraction. He thinks of nothing but her, he's glad for her slap because it was kinder/gentler then being thrown across the hall, and he takes her to the playground late at night and they play like little kids. That's very sweet. Of course he is so smitten that Skinner doesn't care that the children are destroying the school.

Now I don't know how long this relationship lasted, but it seems like they are still in the 'Honeymoon Phase'. So why is Skinner rushing into marriage? Seems rather odd to me, especially since, when he finally proposed, that was when Patty first told Skinner that she loved him and he was surprised and extremely happy. Proposing to a girl you barely know without knowing how she feels about you? Or how you really feel about her? Perhaps Skinner was just desperate to have a real honeymoon; which makes sense, if you consider the fact that he told Edna that he was a virgin.

If on the very extreme side of things, if this was Skinner's first date and he is a virgin then he clearly hasn't 'experimented' like others may have done. So for all he knows, he could be gay and not even realize it.

2. [Bart the Murderer]

Here Willie slaps Edna, telling her to be strong for the children. This could be a reason why he doesn't show much sadness for Skinner after he disappears; when in actuality he becomes very depressed.

3. [Radio Bart]

Principal Skinner cares about his students and his school, so when Willie rushes to help little 'Timmy O'toole' you can see that he really cares for children. Now Willie names his tools, which could be an indication of how lonely he is. And I typically don't like to mention a character's physical appearance, but this is first time we see Willie with his shirt off. Therefore Skinner could be attracted to Willie's muscular body. And Skinner is part of the digging team, so he knows what Willie's chest looks like.

4. [Bart the Lover]

Bart pretends to be a man interested in Edna, but is upset when he sees how sad he made her. So he asks her about the other available men in the school. With Principal Skinner she says that "his mommy won't let him out to play." And with Willie she says "Ugh! I won't even tell you what that guy's into." Which seems to be very interesting to me. For starters, Willie can add some adventure to Seymour's mundane life. And I'm not going to pretend that I know every kink, but if Willie likes what I think he does, then he's the uke and Seymour would be the seme.

5. [Separate Vocations]

So Skinner has a love for the Schools puma statue and it reminds me of Willie's love for his tractor. And even though Bart has Willie arrested, Skinner is too shocked at Bart being an honorary cop, that Skinner could barely react to Willie's arrest.

6. [Kamp Krusty]

So Willie must have already been in Skinner's office when the bell rang. It is possible that they were conversing casually, which would be an indicator of friendship and more.

And I think it's pretty clear that Willie isn't the type to make you feel better. So when he tells Skinner that he did a good job, I bet he meant it whole heartedly. Not to mention the fact that Willie feels comfortable putting a hand on Skinner's shoulder. Touch is very common, but it still shows a level of trust that exists between the two people.

For a brief moment you can see a moment where Skinner looks away. Typically this motion is recalling a memory so it could be that Skinner is remembering a time where he wasn't a very good principal. But for the sake of Wilmore, this could be an uncomfortable moment for Skinner, and that's why he looked away. I can be shy, especially around guys I like, so I often find myself looking away, just like Skinner did. If I am really uncomfortable, I would probably make some excuse and walk away, just like Skinner does.

Plus, did anyone notice the way Skinner winked at Willie and then quickly put on those sunglasses? That could have been from nervous energy. Trying to get away from Willie, he tries to act casual. This causes the wink that makes him nervous/embarrass, so he hides his eyes behind his sunglasses. After all, the eyes are the windows to the soul.

Heh, I kinda love how Willie calls him a "Silk-wearing buttercup". This doesn't seem rude to me, it's incredibly observant though. And I have noticed that Willie says things about Skinner, and it's not really rude, but shows that Willie sees Skinner as higher class. Also, I would totally use 'buttercup' as a pet name Willie uses for Skinner.

7. [Marge gets a Job]

Ok, I really love this scene where Willie fights that Alaskan Timber Wolf. And I think that this is probably a scene that would get mentioned for any pairing that Willie is in. Willie fights a wild animal in order to save Bart, a child that he doesn't really like. So just imagine what he would do/give to protect someone he loves. And I think Agnes would be more willing to share Skinner with someone who could protect him like Willie can. I bet that Willie and Agnes could really get along, now that I think Willie and Agnes could really get along, now that I think about it.

But the strength that Willie displays here is similar to Patty's. Remember when she threw Skinner across the room for trying to get a kiss on the first date? Skinner probably admired it, if nothing else, so if he saw Willie fighting that wolf, then he would admire Willie too. Just imagine Willie protecting Skinner, and Skinner can't help but swoon.

Also, Willie wins the fight, but he doesn't take it too far. In fact he is even kind to the wolf, which I like because it shows a kind, compassionate side of Willie that we don't always get to see.

8. [Mr. Plow]

Hm, interesting. We see Skinner and Willie waiting alone in the school waiting for someone to show up. This alone time could have been a nice opportunity to learn more about each other. I don't know, personally I am much better one on one then with other people crowding me. So seeing Willie and Skinner together makes me think that they really do know each other.

9. [Brother from the Same Planet]

Wow, this is a detail I may never have noticed if I wasn't looking for Wilmore hints. Skinner is sitting at his desk trying to cut back on the school's budget. It has 8 things on the list, along with the cost of them.

1. First Aid: (maybe) $87

2. Books: $110

3. Science: $102

4. History: $150

5. Music Arts: $130

6. Hot Lunches: $99

7. Custodial: $195

8. Playground: $160

Ok, so if he is trying to cut 40% of the budget, I think that's about $413. So Willie does custodial work, and it's the most expensive thing on his list. Skinner could have teachers be responsible for their classrooms and created some sort of system for the bathrooms and halls. He could have worked around Willie and fired him. But instead, Skinner sacrifices nearly double just to keep Willie around. This has got to be something major because Skinner loves his school and being a principal. So if he is willing to lower the state of his school just so Willie could keep his job? What else could I call that, besides love?

10. [I love Lisa]

Willie and Skinner are talking and Willie is honest with Skinner. Being painfully honest with someone can be an attractive quality for some people. But I've also seen times where men are honest about uncomfortable things with people they care about, so those people can deal with it and move on. Also, aside from Willie's honesty, Skinner seems comfortable sharing with Willie about failures. Failures which would make him feel more vulnerable and it would show more trust towards Willie.

Later at the end of the play Willie starts crying and Skinner comforts him without giving it any real thought. I know I talked about how Willie would be Skinner's rock, and that's true. But this scene shows a nice reversal on things. Skinner can be Willie's rock if Willie needed him to be.

11. [Whaking Day]

Ok, so in all honesty, this is the episode where I realized that Willie and Seymour would be a good couple. I realize that there is an episode later where the two kiss for an extremely long time, but no. This is the episode that sealed the deal for me.

Ok, so first of all Skinner talks about throwing away the key he used to lock the trouble students away. Willie doesn't judge him for wanting to do so, but he still explains that it isn't a good idea. Skinner seems to respect Willie enough that it isn't a good idea. Skinner seems to respect Willie enough to listen to his advice, but I guess he doesn't enjoy cursing. Heh, I love how Willie says 'lily hugger'. Perhaps Willie's attention continues to grow with how nice Skinner smells.

Hey I talked about this moment with the Separate Vocations episode, but look at the way Willie is treating his tractor. It is very similar to the way Skinner treats the puma statue. I can imagine myself, or maybe someone else, would write about how Willie and Skinner can both care for the Statue and the tractor. It would show trust and be a good bonding opportunity.

And finally, if the boys they locked away were dead, Skinner was willing to run away and start a new life with Willie. And I don't know about you, but if I was gonna uproot my life and live with someone for the rest of my life, then they would have to mean more to me, then just some guy I work with.

12. [Homer's Barbershop Quartet]

You know, I thought that it seemed a little out of character for Willie to want to be in a barbershop quartet. I didn't think he enjoyed singing since he said 'ACH!' in the middle of his audition. But what if he tried out because he wanted to spend more time with Skinner, or perhaps Skinner requested Willie to try out. This would at least show desire from one or both parties.

Also, since this is a back story, we learn that Skinner and Willie have known each other for at least 8 years. Even if they don't always get along, they got to know somethings others won't.

Plus, wouldn't it be funny for Willie to be an extreme Be Sharp fan? Just walk into his room and it be covered with their merchandise.

13. [Treehouse of Horror 4]

Ok, normally I try to avoid the information given in the Treehouse stories. But the tale 'Terror at 5 1/2 feet' has a moment I often think about with Skinner. He has to take the bus because he is being punished for talking to a woman on the phone. But he feels as if this punishment is just.

Ok, so I feel like this is a regular thing that would happen on the show. Agnes got mad at Skinner for talking to a female on the phone. I was thinking about it, and I thought of 3 different reasons. One, she is simply being over protective of Skinner and doesn't want some girl stealing him. Two, to call he was making was to... um... a professional woman. Or, three, Agnes doesn't approve of Skinner talking/dating women, because she knows that Skinner would be better with another man. She may believe that Skinner is gay and that's why she is so hard on him. Even if she doesn't know Willie, this is a possible reason to explain her behavior.

14. [Sweet Seymour Skinner's Baddasssss song]

Heh, Skinner tries his hand at insulting Willie, but he truly sucks at it. Then he tells Willie to grease up and go into the air ducts. I just think he could have gone or chosen someone who could do it. But maybe he wanted to see Willie all greased up.

Not only that, but Skinner actually seemed excited about flirting with his commanding officer. So if Skinner was willing to flirt with some stranger he didn't really know, just think about how he would behave with a man he has known for years.

15. [The Boy who Knew too Much]

Ok, so in a lot of relationships, there is a more dominant character and a more submissive character. And generally I would say that Skinner would be the submissive one. But with both of them interrogating Lisa, it seems that they would treat the other as equals. Which I think is very important in a relationship. Though this also means that they could switch roles, which is also nice for relationships.

16. [Secrets of a successful Marriage]

Hm, I notice how Willie and Skinner are both in the 'secrets of a marriage' class that Homer teaches. It's almost funny how Skinner can take a class on what makes a good marriage, but his mother doesn't like him dating. But if Skinner and Willie are both in the class, then that at least means that they are willing to settle down.

Well, that is all the examples of Wilmore for seasons 1-5. I hope that you had fun reading this chapter. The next chapter is going to be the character evaluation of Marge in season 1. I know, our first adult. How exciting?