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always or often? Some names are standard w/ ys... like if it's a -lynn(e) name. Linn would look strange to most and I don't think of Lynn(e) as trendy... It's more of an old standard. Also, if it's JUST Alyssa, the y seems more standard than an i, but I agre that in the case of Alessandra, it just looks like someone's trying to be trendy because the y doesn't even make the same sound as the e does... unless you have an accent that really throws off your vowels.