 If you liked
Video Girl Ai
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 ...then you might like
Toradora!
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Both are romantic comedies with similar setups (guy crushes unrequitedly on girl, guy gets help from another girl, guy also helps one of these girls with her own unrequited crush, guy eventually grows to care for the girl helping him, etc) that will tug on your heartstrings. For those who are not fans of the ecchi shows, don't let the ecchi genre tag for Video Girl Ai scare you off. The ecchi moments in this six-episode OVA are far and few between, and of a more mild variety than the more blatant stuff you see nowadays. VGA came out in 1992, after all.