I think Herald has all the Sidestep action figures and when he get’s one of himself he makes them hold hands.
EDIT: Everyone talks about meeting Ortaga’s mom, how about meeting Heralds parents and they get out his Sidestep scrap book.
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I’m feeling this fanart
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Better:
The MC goes to met Herald’s parents and he brings out the Sidestep scrap book.
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Both these are equally likely and I love them both. I imagine momma Ortega struggling to be polite while trying to squirm out of talking about they’re child’s deceased best friends biggest fan.
"Oh you even have coffee mugs, matches the shirt, and-Oh would you look at the time! I have to get going. "
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Oh Herald sweetie (he would, wouldn’t he? Probably ask for an autograph)…I always try REALLY hard not to hurt him too much. I only did it the once accidentally, but that got me the achievement, so I never have to do it again. It’s honestly like kicking a puppy. Hurts my heart.
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Reading the snippet Im reminded why the MC hates him, but also I just see how clueless he is to it. He almost seems innocent, almost.
In one of the shorts it did mention that he got his dirty laundry aired and it almost cost him his career. Hmm look forward to seeing everyone’s dirty laundry getting hung out to dry in book 2.
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People need to use better detergent.
=D
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There are some stains that never come out my dear…
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I can see Sidestep dying of embarrassment before Heralds parents and now I imagine Herald writing fanfiction with himself and Sidestep together. 
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Throw back to our first speculation on Herald being a Fanboy!
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lol that is so very Hearld.
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Dear Diary Journal,
Today Sidestep met my parents.
I showed them my old scrapbook, read them one of my fanfics (the good one! the one mom likes!), and they even signed a picture for me!
It was.
Amazing.
Sincerely,
Me
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I smell a fanfiction
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Herald writes a fanfic of the day Sidestep met his parents?
Yes.
And he posts it online and everyone flames it for the inconsistencies and implausibility.
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Aww poor Herald. He should ask Sidestep to dress up in his old costume as “proof” and take a picture together. Although can’t imagine Sidestep doing that or people believing it really is the former hero anyway.
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They critique him saying he’s missing huge facets of the character and that he made them seem boring
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Yeah and then they go on saying Sidestep is this and Sidestep is that and Herald is not a true fan even though they would never have met Sidestep in the first place.
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No, worse:
Review: herald would never invite sidestep to meet his parents. herald doesn't even like sidestep
Herald: [horrified gasp]
Herald: who told you that??? who told you that lie???
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Could you imagine Herald knitting sweaters with his mom for sidestep in their outfit’s color scheme, and sidestep refusing them ?
Summary
Sidestep: for the last time, I don’t want your damn sweaters!
Herald: sniffs at least have this one
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Oh god, what about the poor MCs who don’t want to make it obvious they hate him and have to accept it to keep up appearances?
And then Ortega’s like:
Ortega: Oh hey, are you gonna wear Herald’s sweater to the get-together tonight?
MC: There’s a get-together? Why am I even invite—wait, sweater??? Shit.
MC: [laughs nervously] Haha, of course!
MC: [internally screaming]
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