What do we think of Valentine for a boy?

My top name for a boy was always William, and I stand by classics like James and Benjamin. My husband LOVES William with nn Will but our last name is a single-syllable name that starts with W. However, I'm pretty averse to the 'superhero' alliteration and basic naming of Singlesyllablestrongfirstname, Singlesyllablealliterativelastname.

I recently brought up the name Valentine after working with a student named Valentina. We're both very pro-gender neutral names for girls but I was pleasantly surprised about how intensely he loved Val for a boy when it was inspired by a little girl. I LOVE it for me but I'm concerned he or our families will second-guess it when the time comes.

He equates Val with Will as being strong, virtue-based names (Valor!) I DO like that Valentine more with our last name than Will, even though Will would be 10/10 for me without that consideration.

However, I'm worried Valentine is a little out-there for a boy in the modern world, especially with my parents being conservative midwesterners and him being the son of immigrants from two separate continents with very specific tastes. All his siblings have names and nicknames from multiple languages and he's always hated anything hard to spell, interpret, or need to repeat for any reason, so because of that experience we have to go simple.

Thoughts?