" A fan of Durarara once asked a creator Ryoga Narula if Izaya ever had any past love experience, he responded by saying that if he were to answer that question it would be a bit of a spoiler. This left many fans wondering that perhaps it was the character Namie it was later stated that Izaya abused Namie as a house wife rather than a friend, but holds no romantic feelings towards her, even going so far calling her an awful person. In the novels he himself mentioned that does not hold any attraction for any individual, except for one, dubbing himself kinda a sexual. Though there are big hints that point that he already has "something" with the character (Y/N) (L/N).
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They known each other since Elementary, but soon (Y/N) had to move, once 12 years had pass she comes to Ikebukuro. Izaya was excited to have his "toy" back. Also People who known Durarara for a while may not know he took (Y/N)'s virginity meaning they had sex, sorry Shizaya's fans. But why would Izaya have feelings towards (Y/N)? Well for starters his English voice actor 'Johnny Yong Bosh' and (Y/N)'s voice actor '(Your real Name)' are actually together in real life. Big coincidence! Another reason is when she's hanging out or talking with Shizuo he gets a weird unpleasant feeling. Asking Namie what's this new feeling she states 'he's jealous' but he denies that. One time when (Y/N) was baking a cake she got icing on her face, when Izaya came in the kitchen he licked it off her cheek, results were a tomato (Y/N). He also likes to call (Y/N), (N/N)-chan, she gotten that nickname from the character Kasuka Heiwajima. Right now I'm still waiting for one of those two to confess. I'll make some facts about (Y/N) in a video some other time."