Chances are likely that he did, or at least had a very, very close relationships with her when he was living.
Evidences are spread all over the manga - the fact that Road has fallen in love with Allen strangely at one glance (Allen is the possessor of the 14th Noah, Nea), another fact that she was the only one with Millennium Earl that survived when Nea assaulted the Noah Family, and that her stepfather is raged at his assumed relationship with Road and Nea Walker, torturing Lavi for Bookman to spit out the truth.
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Yes, she kisses him and saves him twice in both the manga and anime.
Ta Nea tis Megalopoleos was created in 1951.
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The cast of Conditional Love - 2009 includes: Hunter Gomez as Trent Walker Wendi Wendt as Wendi
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