I cut off the exes that ridiculed me

Vol. 2 Chapter 11: By train.

"Wow! I'm amazed it takes less than three hours to get to Kyoto. Modern technology is no joke."
"Thought it'd take longer as well."
It's the standard for something to go wrong whenever we prepare to leave, but everyone got to the meeting place in one piece. On-time to boot. From there, we boarded the bullet train and killed time by chatting all the way to Kyoto.
However, unlike any other outing where the main topics would be about clothes or games, our main topic was Katayama's love life. We sat down and had an in-depth meeting about it. Unfortunately, the pair sitting right in front of our row was composed of Iwashiro and Asakawa, so Katayama and I talked in hushed tones.
"...So, how many conversation topics have you prepared for her?" I asked him.
"Five about fashion, eight about recent tv shows and movies, four about manga and anime, and six about trendy sweets."
"That's great. Do you have that many ready to go inside that noggin at all times?"

"'Course I do. I'm still afraid it's not enough, though."
The fact he had twenty-three conversation starters inside his brain—at the ready, mind you—was enough to convey how serious he was about all this. With that much to talk about, it wouldn't be surprising if they went weeks on end without stopping, maybe even more if they keep going with it.
...There's just one problem, though.
"Yeah, but you don't know what she likes besides clothes, dude."
"As expected of my bro, that's it. I just need one more topic I can definitely get excited about..."
"Or better yet, a conversation that nudges her into recognizing you as a member of the opposite sex."
"...Yeah, that'd be nice."
While it is important to be excited about stuff, you need the other party to recognize you as a potential love partner so that they'll change the way they approach you in the future. If you're not even seen as a man, anything past and including holding hands is nothing but a criminal offense. Creep behavior in general.
However, if she recognizes you as a man that she's interested in, holding hands may be used as a trump card to suddenly shorten the distance between you, breaking that initial barrier.

In other words, making a reckless approach in a situation where you're uncertain of how you're seen by others is like trying to grasp at straws while being blind. One wrong move and you could end up with it on your nose.
That's why I have to know what she thinks of him at all costs... And there's a way to do just that.
"I'll ask Asakawa to casually ask her that."
"Can she do that?"
"I'll send a message regardless."
I turned on my phone and asked Asakawa about Iwashiro's preferences for guys. I decided that it'd be impossible for her to ask what she thought about him specifically since we were in the row right behind them.
As soon as I sent the message, I heard her phone's ping play right in front of me. It's usually bad manners to have your notification sounds on in public, but since Asakawa's always communicating with her manager about her work, it's understandable. I myself put mine at a minimum so as not to disturb anybody.
After about ten seconds, I felt my phone vibrate in my hand.
"Okay, I'll talk a little louder, so listen as quietly as possible."

I showed my phone's screen to Katayama, then we started listening in carefully while feigning a random conversation about something.
"...Speaking of which, I'd like to get closer to Miyamoto-kun during our trip; can you help me with that, Iwashiro-san?"
"Okay, it's a promise. So, what's the plan?"
"I don't have anything in mind right now, but it'd be nice if I could sit next to him or something."
"Got it. I'll do my best"
I wondered what kind of promise was Iwashiro's, but I don't have the time to devote my thoughts to it right now. I continued listening to Asakawa's words.
"Thanks. Hmm, that makes me wonder, is there any guy you like? If so, I'll help you!"
"M–me? ...I don't have anyone like that."
"Hmm, I see. What about someone that you're interested in? Or someone your type?"
Way to go, Asakawa! Keep it up!
I glanced to my side and saw Katayama smiling while trying to find out what the girl he liked, liked. His smile was more like a snicker, and though he still looked handsome, he was on the verge of stepping into creep territory.
As I brought my attention back to the row in front, Iwashiro spun her next words gingerly.
"I, I like fashionable people..."
"I see... Oh! Katayama-kun is fashionable, isn't he? Do you think so too?"
"T, they'll hear you!"
"Don't worry, the two are having a conversation right now so they can't hear you!"
Asakawa, a.k.a the schemer, has wonderful conversation skills. Her follow-up may elicit key information to be drawn out; more than I'd expected. We started talking a little louder about a game as Iwashiro glances back.
As soon as she thought she was clear, she swayed in her seat slightly, and we focused more on their conversation.

"I, I think Katayama-kun is fashionable..."
"Yup, I know! Are you interested in him?"
"T, that's... I'd be a nuisance if I did."
"I see... Well, I think you two suit each other fine."
The conversation seemed to break off there, and silence returned to the seat in front of me. Meanwhile...
"Yo bro, is that a pulse?"
"You think so too? Oh my God, I think I'm gonna start running."
"Don't be afraid. Iwashiro-san seems rather reserved, or rather, she seems to have very low self-esteem."
She said she'd be a nuisance. Well, if I were a girl, I wouldn't think I'd be a match for Katayama, who shines bright as a star. But even so, I don't think I'd use words that would demean me.

From this, I could take a very educated guess and say she has some problems with popular people, or rather, that she's afraid of them.
"Hmm, if only I could get her to trust me more..."
"That's right. Let's build your conversation during the trip around that."
"I'll try. Thanks, bro."
Checking the time on my phone, I see that we have about one hour until we reach Kyoto. Let's rethink our strategy in the meantime, preparing for the coming war.