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Gary Gellar is the son of powerful businessman Willis Gellar and army lieutenant Berry Gellar. Gary tries really hard and never quits, but just can't seem to catch a break. He dreams of one day being famous and idolized, falling in love and marrying his dream girl, and changing the world someday. But Gary is unpopular and cursed with bad luck, at the moment. Most girls don't like him at all, with the one exception being Rain Leary, his one and only friend (who may or may not be Bisexual or a Lesbian). He currently lives with his aunt Tamara, the little sister of Gary's mom, Berry, as Gary is in Moonlight Bay to attend boarding school.
Gary is the nephew of Tamara Riley, from his mother’s side. He and Tamara get along very well, unlike his strict and aggressive parents, Berry and Willis, whom he has a somewhat-high negative relationship with. Gary has a somewhat positive relationship with housemate Anna Pinkerton and is just at the Friends barrier with her. (But because Anna has the Super Friendly charisma skill, this will never fade away.) Gary used to be really Good Friends with Moonlight Bay neighbor Alia Zhang, but feels betrayed by ever since she outgrew him while he was still in high school. Gary resented this and felt abandoned by her, thus promptly breaking off their friendship, even though Alia felt confused by this, as she couldn’t help growing up, never felt like she stopped talking to him, and even had romantic advances towards him in high school. (In fact, had Gary been more patient for another two weeks and waited to catch up to her, Alia might’ve been willing to WooHoo him). If anything, Alia has more reason to feel saddened and betrayed. In high school, Gary never had any real friends, except for Alia and Rain Leary. Rain Leary is Gary’s Best Friend (ranging close to “Best Friends Forever” status), but because everyone in Moonlight Bay is convinced Rain is a Lesbian, even though she assures everyone she’s not, things have never gone beyond the Friend Zone. Gary soon hit the weights a lot and improved his Logic skill, somewhat drawing the attention of kind and spiritual Rita Nelson, who never really noticed him in high school. Gary remembers the Nelson sisters, especially considering how he’d always used to get beat up and shoved into lockers by her twin sister, Sofi. Gary soon became the boyfriend to the attractive, tall, and blonde Rita Nelson. And although she’s nice enough and a really Good sim, Gary’s mostly with her because she’s the first and only girl he’s ever been with and kind of thinks she’s the only one who he’d ever be able to attract. As Gary dates Rita, however, Rain is secretly jealous, as she really wants to be with Gary. As the relationship grows and Rita has started thinking about becoming engaged, Gary has learned to tell her apart from her evil twin, Sofi. Considering Gary and Sofi are Old Enemies, Sofi hasn’t been above using her looks into tricking Gary into a night of WooHoo, only to embarrass and humiliate him halfway through. Luckily for him, Gary is able to tell them apart by now and Sofi’s latest prank never made it off the ground. Although Sofi seems to hate Gary for no reason other than being an evil b--ch, she really secretly resents their relationship together and feels like she’ll always be alone and that no one will ever love her like they love her sister. Sofi’s also been jealous of Gary’s cleverness and intelligence since high school, wishing she was nearly as smart as he is.