LucarioTheSuperSaiyajin
Hakaishin
I think the roadblock is Ash views all his female companions the same way. If anyone in-show ever asked Ash which female friend he liked best, I bet he wouldn't be able to say or would say something like, "I like them all equally."
Ash isn't the type of person to show preference especially romantically for a female.
So I think the "last minute strategy" Serena would use in order to make Satoshi show preferences to her, is to make a big sacrifice or make something that leaves a very strong and unerasable impression on Satoshi: Generally, overly dense, "widowed" or uninterested in love shounen characters (with the exception of certain Saiya-jin) are paired up with the woman who does nothing or doesn't stand for herself in the series, but she makes something very important to the main shonen lead that makes him to notice her.
Some examples in anime/toku media in spoilers
For example: In that Choujin Sentai Jetman tokusatsu series there was White Swan/Kaori who stayed with Red Hawk/Ryuu after Radiguet's defeat and make him forget about Rie's loss to the point they were married in the 3-years timeskip ending (well, the white ranger had a crush... ahem: she was in love with him despite red hawk didn't reciprocate her feelings cuz that Rie thing until the 3 years-timeskip in the final chapter. There was in the middle that G-2 Joe Asakura ripoff Black Condor/Gai who lusted after White Swan, got into arguments and fistfights with Red Hawk because of that love triangle thing and eventually they were dating until near to ending cuz they were very different). And in Inazuma Eleven 1st series, the main chara (Endou Mamoru) was a total dense (insert bad words here) who was unaware of Aki, Natsumi and Fuyuka's feelings towards him. However the "oujosama" (Natsumi) discovered Endou's grandpa was alive (he believed his ojiichan was dead) and he was thankful of her for that thing (they appear married at IE GO ep. 18). There are more examples in other "aimed at children" animes and tokusatsus.
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