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I dont think Jessie was ever pregnant in the show.

Let alone four times in a row. Something tells me she´s got a membership card at the abortion clinic.

Base +8, Zblayde -6, Yossarian762 +7, observer1980 +21, kondoriyano -6

I know it may make her look any old, generic anime girl, but i love Jessie with her hair let down. It's much sexier this way!

Base +11, Yossarian762 +7, swordpaladin +9, Zblayde +6, bongzilla +6, Epherion +7, Zerokun-san +7, Megaton +42, GuniPadla +6, Saint Heaven +6

that hair made her sexier than ever before

Base +6, daicalun07 +6, Epherion +7

@Darkestvamp: If she was ever pregnant, it likely wasn't by James. The anime would have us believe that not only is he not interested in women at all (unless he's dressing like them), women who resemble Jessie (and Jessie herself) absolutely terrify him. If anything he's far more attached to his Pokemon. And funny how his old ones tend to leave eventually... possibly to have their human-hybrid babies off-screen. Because those are the only kids James could have at this point.

Unless Jessie rapes him, and she's angry enough often enough where I wouldn't dismiss it. Though why would she do that just to have repeated abortions? I know they're often broke, but steal a pack of condoms for crying out loud. Or don't rape your arguably gay best friend.

Base +21, Zblayde -6, merkmuds -6

In the Electric Boogaloo manga, Jessie and James get married and Jessie becomes pregnant in the end and one of the pictures is clearly based on what James looked like at the time.

Base +6, kondoriyano +6, merkmuds +6