Do you think its weird that I name my son Oliver

I think Oliver is a lovely name, but with your name being Olivia, you will definitely be having to answer questions all the time. If you`re fine with that and dealing with people`s unvoiced judgements, then I would go ahead. But you already sound a bit hesitant....
So if you love it, go for it. Your son will have the name for the rest of his life, and I don`t think that you will always be behind him introducing yourself.
 
you'll end up meeting both types of people (for and against). in the end, just go with whatever you like, as he's your son and not other people's!

my brother and i have similar names as well, and we've had to explain it to TONS of people, and i've gone through a phase where i hated my name, but now i've come to love it.

and now my husband and i have similar names and i've had idiotic people asking me 'did you change your name to suit your husband's?' which i just laugh off and ignore.

just go with whatever you love. but personally i wouldn't use tom and jerry either, middle/high schoolers can be cruel. I had a classmate named diana in HS and one of our teachers kept calling her 'here comes princess diana' which i don't think she was too fond of.
 
To give a biased opinion...I recently gave birth to a baby boy and we called him Oliver. It is a beautiful name!
 
but then again, no matter what names,, kids can still be cruel.. so what the heck.. :)
if it is not about the names, there is always something to be cruel about..
hmm.. michael and jackson is a bit weird though. i hope they are not twins..
 
Yup it does sound a little bit weird since your name is Olivia, cute for now but won't be so much once he is a grown up man. Otherwise Oliver is a lovely name :)
 
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