Head vs. Heart: Which rules your name choice?

We were intrigued by the question posed on the forums by jackal, who loves the name Ingimar, well-known in her native Iceland, but wonders whether she should give her son-to-be a name that travels more easily, like Robert or Matthias.

Jackal’s question came down to head vs. heart: Which is the best way, the right way to choose a baby name?

Of course, if your heart and head align in your name decision, that’s the ideal.  But often the name we love, the name we want in our gut has some issue: it’s hard to pronounce or it doesn’t work with our surname or our partner doesn’t like it or we fell in love with it long ago but it’s since gotten too popular.

And then our head steps in, proposing the name that flows better, or the name that is immune from teasing, or the name that honors your beloved grandpa even though, ouch, Floyd…

Have your head and your heart wrestled over a name choice?  Which won, and why?  And what advice would you give to others in this common predicament?