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I don't really like them together for some reason. Maybe it's because I'm not a huge fan of sibsets with names that all start with the same letter.

I quite like Holly. Holden isn't a personal fave but it's not bad. I don't think the names are "matchy" in the way of being too similar to one another but I did notice that saying "Holden and Holly" aloud, with the vowel sound of Holly being similar to that of the Salinger character's surname, Caufield, made my association to the novel even stronger.

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I think your chosen middle names are very nice. Some other ideas for Holly I was playing with recently...

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Holly Abigail
Holly Danielle
Holly Guinevere
Holly Isobel
Holly Jeanette
Holly Miranda
Holly Winifred

I don't normally like twins with the same letter for their fn's, but these names work together as they aren't too close in sound.

Nah. I dislike matching twin names. Well, sometimes. If I really like the two names together I probably wouldn't care. All four names are dated so they have an icky flavor. I do like that Holden and Holly don't sound very similar; how the Hol-beginnings are different enough.

very nice!

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I think those are very nice combos. I don't think they're too alike, since they have different "o" sounds. They're modern-sounding names without seeming (imo) too trendy

I'm not a fan of Holly, Holden is not my style, but I like it best out of the two. I think they're too matchy for twins, Holly could practically be a nickname for Holden (if it wasn't a girl's name).

I'm not crazy about either name, but I think that together they strike the right balance for twins. They start with the same three letters, yet the first syllable is pronounced differently. It's a right balance that says, "They're twins and we think that's special and we want it recognized but we realized they're different people!" A balance that's hard to achieve.

I really like Holly, I have a cousin named Holly Noelle who was born close to Xmas.
I don't like Holden, it seems so stiff and at the same time soap-opera character. Holly and Holden also seem too matchy-matchy.

Holden and Holly are fine for twins. I think Jennifer as a middle name is interesting.