Jessica has dated all the boys at Sweet Valley High. Well... almost all of them. Past boyfriends include: AJ Morgan (a generic nice guy), Ken Matthews (the quarterback of the football team and her best friend's boyfriend), Sam Woodruff (her ~one true love~ who died in a car wreck), Todd Wilkins (who was also her sister's boyfriend and he later becomes her third husband!), some guy named James who was murdered by a serial killer, Christian Gorman (who hit his head in a pool and drowned), Professor Miles (one of her teachers), Jonathan Cain (a fake!vampire who was actually a serial killer), Mike McAllery (her abusive first husband-- yay 18 year olds getting married!), etc. etc. This girl has terrible taste in men and it shows. Bad life choices all around.

City-wise, she went out with Harry Osborn for awhile before he was ported out. She also flirted with Gerry a bit. And then Jason showed up and she declared herself to be his girlfriend (though he probably would not agree with her assessment of their relationship.) and at this point he's finally agreed to this assessment. They have a romance based of manipulation and jealousy and hormones, and weird attachments to each other and it's totes not healthy but they're 19 so who cares.

Having a boyfriend doesn't stop her from flirting with everyone though. She's sexy and she knows it, so look out all you hot guys she is totally going to try using you for her own gain.