Now I know the comics usually like to pair Reggie with Veronica or Cheryl (yes with Cheryl. It's a rather adorably funny story called Love is Nasty and I actually really like them together most of the time as sort of an evil power couple because they bring out the worst in each other but I digress).
But now, I suggest Reggie and Alexandra now because they have so much in common.
1. They both feel second best
Reggie's main thing is because he wants to the top dog, school president, lead in plays, get the girls and of course, scheme to make the Archies, the Reggies. When the comics try to show Reggie's sympathetic side, they show how he hates that the town loves Archie's nice guy attitude so he plays up his bad boy prankster side. Why join them, when you can prank them. Meanwhile, Alexandra loves to be the star of every occasion and schemes to make Josie and the Pussycats be Alexandra's Cool Cat Band with her as the lead singer of course (despite being gone deaf). Not to mention scheme to steal Alan M. from Josie just so she can be number one. Also very very subtly implied that she does it because she's lonely. But that's very rare. Like Reggie, she prefers to hype up her rich beauty vibe to show why she's better than Josie.
2. They both love the expensive, flashy things in life
Reggie's known for his awesome, speed racing cars, nice threads and flashing concert tickets and the like he can get with his money. Though sometimes he's cheap, he will use them to beat other men to get the girl. And Alexandra Cabot is just the same, only richer with mad inventions and castles and in one story, their own kingdom Cabotopia. So together, they would have such lavish dates in Reggie's Mercedes and dining on gold plates.
3. They will respect the other's nasty streak
Like I said before, the two can get into pretty nasty tricks to get what they wanted. As a result they've been cast as the town villain. While they mostly embrace the role, they're also lonely. So it would be nice for them to have someone who wouldn't judge them automatically for such bad actions. Hell, they'd probably add suggestions.
4. The egoism
These two are the most self obsessed, egotistical people in the Archieuniverse. Mirrors are one their best friends. Imagine them goading each other with "The most gorgeou boyfriend in all Riverdale," "You're right, you should be the star of the Pussycats." Ugh, they wouldn't fit their heads through the door. Or more likely, they start fighting over whose richer? More beautiful? More mirror time etc.
5. Power couple
Do I really need to explain this one?
More ship ideas underneath including CherylxAlexander and JasonxVeronica.
Alexander Cabot III and Cheryl Blossom: Cheryl wants to be a star. Alexander wants to manage a star. Ya see what I'm getting at here?
I mean Alexander's infamous for all the stunts he tries to get the Pussycats roped into like million dollars stadium tours across the world with high rise podiums, special effects and back up dancers that eventually the Pussycats quit because they prefer to be lowkey rockstars. Or when he tries to make them wear dresses made up of CD discs to boost sales.
Or when Archie and Valerie got married, trying to hire a reality show to boost popularity. He’s all about the flash and publicity and of course, money. He can be scheming and lowdown in his pursuit of fame, really representative of the sleazy Hollywood manager.
And Cheryl.. the MTV house renting, temporary Sugar Girls member, burlesque dressing, reality tv show hanger on, she will do anything to get the attention on her. Even making the Cherry Blossom Festival to the Cheryl Blossom Festival. The girl's outrageous and can be as lowdown sneaky as anyone whether it comes to attracting boys or screwing with Betty and Veronica.Cheryl would have no problem fulfilling Alexander's ideas, in fact she'd encourage it. Together, I have no doubt they'd get their wish for fame and fortune.
Jason Blossom and Veronica Lodge: Even though Veronica is usually paired with Reggie or Alexander, she's rarely been paired with the the third bad boy of Riverdale. But why not once more for old times sake?
I can imagine the drama already that at first with Archie and Betty paired off with Valerie and Trey so Veronica pairs up with Alexander Cabot.
But this may not be the last affair as many might think, not only because Veronica has some amount of class and won't go for all of Alex's crazy schemes even if they will get publicity. Veronica has shown to be snobby and actually reject Alex (for laughs of course) by saying he was poorer than the Lodges. See here.
But much more likely, Cheryl, looking for a challenge, steals Alexander away from Veronica and Veronica in revenge, decides to date Cheryl's brother. Of course, this all starts as revenge and a prank which Jason plays along with because it drives his sister crazy. But slowly they become the mask as they fall in love.
In the comics, Jason has a mega crush on Betty who doesn't reciprocate because of the Archie factor and because Jason can be as mean and nasty as Reggie. Though for Betty, Jason seems willing to change into a teddy bear if he could be with her.
What I'm basically getting at is that Jason has a soft side for the girl he loves so when he falls for Veronica he falls hard, and I think Ron would appreciate this sweetness only shown to her. Plus the devotion compared to Archie's wishy washiness. Not to mention, Ron would like a man who easily fulfills his whims and has the money to match hers. Also he has Betty trunks, I bet she’d want Jason to have a whole outfit with her face on it.
Also just imagine the drama! Cheryl and Veronica as sisters in law! Alexandra and Cheryl teaming up as BFFs again! The money, the fame, it would be ridiculously fun.