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In Ramona's Not-So-Epic First Kiss, Ramona develops a crush on Bobby after he gave her a kiss, which turned out to be her first one. When she attempted to pursue a relationship with him, it turns out he was already dating another girl named Bethany. When Ramona and her friends plan a group trip to the movies, she ultimately leaves early due to embarrassment.
Bobby and Bethany break up in Girl Talk. Shortly afterwards, Bobby attempts to ask out Ramona again in front of all his friends, but she denies him. In retaliation for embarressing him in front of his friends, Bobby uploads an embarrassing video of her on YouTube (although she initially thought Jackson did it).
Jackson knows he was responsible and sets up another embaressing video to help Ramona get payback.
In Happy New Year, Baby, Bobby visits Jackson for the New Year's eve party. He wants to share a kiss with Ramona, but Ramona doesn't seem interested. Later on, he convinces her, and the two share a kiss.
In Season 3, it is revealed that the two begin officially dating. He gives Ramona a hickey which she attempts to hide from her parents, although Kimmy finds out anyways. The two go on dates and hang out in general.
In the latest episode, Bobby writes Ramona a poem before she leaves to Japan for Steve’s wedding. ‘Dear Ramona, I love your brown eyes and your teeth are like pearls. While you’re away, can I see other girls?’ He says seeing other girls will ‘ease the pain’ of living without Ramona. She is angry and says she put up with his selfishness for too long. She explains the relationship was one-sided and she deserves respect. Bobby doesn’t understand, and Ramona responds using 'Popko style'. ‘When we first started dating, I was totally pumped! But as of right now, you’re officially dumped.’
At first, Ramona is a little hurt. When Kimmy attempts to cheer her up, Ramona reveals she is hurt because she treated him with kind and respect, but she deserved someone who treated her as an equal. However, she says she did the right thing. Kimmy encourages her to cry, which she originally declines because Bobby never treated her right. She eventually starts crying since Kinmy forces her to in order for Kimmy to cheer her up.e