In an exclusive clip from her TLC series, I Am Jazz, Jennings is planning a fun night with her friends when the subject of inviting boys comes up, and Jennings visibly squirms.
"Being transgender has completely turned boys off from liking me," Jennings says.
In the past, Jennings reveals she's had a "pretty rocky relationship" with boys, including bullying and alienation.
"This one time this really cute boy liked me," she explains, "and then once he found out I was transgender he started calling me 'chick with a d---' behind my back."
When her friends are embraced by guys, Jennings admits that "sometimes it hurts" to be ignored.
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Still, Jennings told PEOPLE that "being transgender is the process of learning to love yourself and accept your difference."
Other people "don't define me," she said. "I define myself."
I Am Jazz airs Wednesdays (10 p.m. ET) on TLC.