This is the only summary I've ever found on Dylan's dating history
>Examination of police reports and Dylan Klebold’s journal indicate that Dylan did, briefly, date a Littleton High School student in October of 1997. The relationship consisted of only a few dates and then the girl broke up with him because she felt “*there was something strange about Klebold and she felt uncomfortable with him.*” A few weeks later, the same girl began a 4- month courtship with Eric Harris. Klebold referenced his relationship in his journal on 10/14/97, after the pair had broken up. In a rambling entry, Dylan despaired that he did not find the happiness that he was seeking in this “phony” relationship and wished that his real crush, whom he believed was his one true love, would feel the same way about him. Despite his protestations that their love was not “true”, the break up with this girl seemed to affect Klebold deeply. His writings on this day reveal his profound sadness and desire to end his life.
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>It is the only dating relationship that Klebold is known to have had. Dylan did ask a few other girls out but was turned down. A few years before the shooting, he had a crush on a girl that he communicated with online. Klebold asked this girl for a date but she declined, so he did not continue to pursue her. In one instance, a girl Dylan was interested in worked at Southwest Plaza Mall. After she declined his date request, Dylan “*stated words to the effect of, “Maybe I’ll ask you out again*.” A friend of Klebold’s also tried to set him up once, but that girl said no, as well.
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>After the shootings, several students told investigators they felt that Robyn Anderson had romantic feelings for Dylan, but that these feelings were not reciprocated. Klebold’s parents told police that while Anderson and Dylan were friends and often studied Calculus together, they didn’t feel that Dylan considered her to be his girlfriend. It is likely that Robyn also viewed the relationship platonically. In a letter penned to a friend of hers before the massacre, Anderson told how she had convinced Klebold to attend the prom with her, even though he had no real interest in going.
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>“*I couldn’t decide who, if anyone, I wanted to go with, so finally I convinced my friend Dylan, who hates dances, jocks, and has never had a date let alone a girlfriend to go with me! I am either really cute or just really persuasive! I think we will have a good time though because we always have fun when we hang out. He’s a blast as a friend, but I guess it will be kinda wierd to be out with him all dressed up because mostly when we do stuph we just go bowling, watch movies, or I help him catch up on the calculus assignments he waits until the last night to do all of. So, point being, I figured it would be better to go with someone that I know I will have a good time with, but won’t expect anything than someone that I half like that half likes me where who knows what the night could bring. See my point? Of course if you were in town I would take you, but I didn’t figure you would be.*” After the shootings, Anderson re-emphasized to her friend that she and Dylan were not an item in an e-mail in which she wrote, “*oh, and I wanted to let you know to only believe half of what the press says… cuz I was never Dylan’s girlfriend- I asked him to go to prom with me as a friend and he did it as a favor- I didn’t want to go with someone that might ditch me or would end up being a jerk all night- I knew that we would have fun cuz I always had fun with him.*”
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>The majority of Dylan Klebold’s romantic life apparently revolved around an unrequited love.
The Littleton High School student was Sasha Jacobs. The girl he talked to online was a Columbine student named Sarah Slater, the girl he asked out at the mall was Tobin Kennedy, and Devon Adams tried to set him up with Kayla Kathol.
