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I love the name Ian, great choice! When I was pregnant with my son, Wyatt, our other top contender was Ian Maxwell...so I like that a lot!
I like names that don't start with vowels and don't start with N to go with Ian.
I like Connor, but my husband shot that one down. I also like Nathaniel. Not sure how I feel about ending with N and starting with N, but it doesn't seem to hurt the flow too badly. Alexander could also work. I like the idea of a longer name, since Ian is so short.
Honestly, I think Ian sounds great with a number of names! I don't think it needs a long middle name, but I get why you want one.
I like the suggestion of Ian Thomas. That's really nice!
Ian Alexander has too many 'N' sounds to me and Ian Nathaniel sounds like it all runs together since Ian ends in N and Nathaniel begins with N.
Ian Hunter Jeffery
Ian Bradford Jeffery
Ian Tanner Jeffery
Ian Chandler Jeffery