Last year-ish. Was a brief thing. Mean people said Ian just wants a piece of Ashley's Twilight fame. Whatever. Now with TVD Ian is more relevant than Ashely who gets to date that Jonas dude.
About the Ashley and Ian thing, they weren't actually dating. He does have a long term girlfriend after all whom he has been with for years. Not many people know this but The Vampire Diaries filmed their Pilot Episode up in Vancouver during the time that New Moon was being filmed so Ian just went to hang out with an old friend aka Ashley. (they have both cleared up that rumor in interviews in the past)
I thought he and that long-term GF (Megan or Maggie) separated because of "complicated situations" or something like that. I think she's the one who slept in car while he drove and rehearsed for Vampire Diaries audition, the story that always in all interviews.
Whatever, it's not even remotely as interesting as the Nina+Ian rumors. It's so funny how she and tons of other people call him Smolderhalder (which is unrelated to anything, just funniest nickname ever).
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