Him dating others or starting a family could happen but I personally dont really see that taking place as it was never implied. But thats just me ! Im not the writer.
Long distance relationships are hard for adults, so imagine getting through one as teenagers.
I made a post similar to this a while ago, but I came up with new details/ideas.
In the summer of 1992 (since people loved the summer vibe in season 3 so much), almost 5 years since the events of season 5, 12/13 year old Holly and a couple of her friends (including Derek) will discover that the Upside Down somehow still exists (despite them ending it in the season 5 final).
There will be 6-8 episodes. One of the episodes will be titled “Dear El”.
The Upside Down coming back will represent what happens when you suppress your trauma/emotions.
Holly will call Mike, who has just graduated from college in another state, and ask him to help them since she knows he has experience with this stuff.
Mike’s hair will be long and tied into a bun (like Eleven’s in season 5), and he will have a tiny beard/stubble. It will be heavily implied that he has been to rehab at least once for drugs or alcohol.
This spin-off will revisit some of the iconic places from season 1 (the train tracks, and the ledge where Eleven saved Mike).
Dr. Kay and Sullivan will be involved somehow.
There will be some comedic interactions between Mike and Derek (they will basically become the new Steve and Dustin).
They will tease a possible romance between Holly and Derek. Holly will struggle to say “I love you” like Mike and Nancy. There will be a scene mirroring Nancy asking Mike if he liked Eleven in season 1, but it will be Holly and Mike this time.
“Do you like Derek?”
”What? No!”
Mike will encourage Holly not to hide/suppress her feelings.
Nancy might make a brief appearance, so all the Wheeler siblings can share a scene together.
There will be a couple emotional scenes with Mike showing just how strong his guilt is for building the bomb that “killed” Eleven and not thinking of a better plan to save/protect her. He will carry around a notebook wherever he goes and refuse to let anyone look inside it. We will also see that he has become really good at coming up with great/smart ideas/plans.
Example of emotional scene: They will walk in the woods near Maple Street and Mike will start to cry. There will be a flashback to when he and Eleven met there in 1983. He will put on sunglasses to hide the fact that he’s crying.
Eventually they will realize the Upside Down will never truly die, but they can cut off its contact to the real world permanently. It will require someone to pull a lever or something like that (I haven’t really thought it through.) But there is a problem - they do the math and realize the person wouldn’t be able to get out in time.
Holly will try to think of a way to pull the lever without a person so no one has to die.
The narrative will convince us, through dialogue and certain camera angles, that Mike is suicidal and is secretly planning on being the one to sacrifice himself.
Holly will think she knows what Mike is planning to do and confronts him. She will have a heart-to-heart with him (it will be similar to Hopper’s speech to Eleven in the season 5 final). Mike will promise Holly that he’s not going to die.
Mike will get his Mike The Brave sword fight moment.
In the final episode of this spin-off, they will do everything they needed to do, and they will leave the Upside Down and celebrate. Then they will realize that Mike is not with them.
We will see Mike standing by the lever, still in the Upside Down.
Holly, Derek, and their other friends will be crying and begging him not to do it, Mike will be crying too. He‘ll tell them to tell Karen, Nancy, and his friends that he’s sorry and he loves them.
Right before this happened, Mike gave Holly the notebook he has been carrying around the entire spin-off and insist that she keep it for herself.
Mike will pull the lever (maybe similar camera angles to when Eleven “died“), the Upside Down will disappear, and so will he.
There will be a time skip of a few days (maybe weeks), they will show Mike’s memorial with Holly, Derek, Karen, Nancy, Ted, and all of Mike‘s friends attending.
When Ted almost falls asleep at the memorial, Holly and Nancy will call him out in front of everyone for being a terrible father.
After the memorial, Holly will go into her room and open Mike’s notebook, curious to see what’s inside and why he wouldn‘t let anyone see it.
Inside the notebook, there is a postcard tapped to a page with a photo of three waterfalls on one side, and a note on the other side. The note reads: Maybe one day you will find me when the time is right. As Holly flips through the other pages, she will find blueprints and a full plan for Mike to fake his death, involving a trap door or secret tunnel. Holly is smiling as she realizes her brother is alive. On the last page, there is a handwritten note from Mike to Holly. In a voiceover, Mike apologizes for leaving everyone, he tells her he “Had to go see about a girl.” (Good Will Hunting reference). He promises Holly she will see him again one day when it’s safe.
We will get a montage of Mike escaping, getting a fake ID, traveling on a small plane or boat to Iceland, cutting his hair and shaving his tiny beard/stubble, arriving in a town, talking to the Icelandic town folks, and finally walking up to a cottage where Eleven lives.
Leaving Holly the only one who knows Mike is alive.
”Ain’t No Mountain High Enough.” By Marvin Gaye and Tammi Terrell might play in the credits.
What are your thoughts?