Has anyone ever noticed that the structure of Marry Me a Little is a little redundant? ...Or is there something I'm missing?

I feel like we hear about this guy who decides he is ready now. But that the second chorus doesn't add anything. It's weird because the song builds up to "I'm ready! I'm ready now!" and then just goes back to the beginning.

Unless the idea is that Bobby gets all excited, thinks he's ready, gets scared and has to build up again to certainty?

If you see some writing in lyrics that may have a "hidden" message, then it is usually done so on purpose by the lyricist. Although I don't see what is so special with "Marry Me a Little" being the redundant song in the score of Company. Don't get me wrong, because Company is my all-time favorite show, but the almost every song in the score is redundant, but it doesn't really matter because each time the melody "repeats" itself it does so with new and very clever lyrics that really get the characters and the "philosophy" across.

But a general rule:
"If you find something clever in a lyric or melody of Stephen Sondheim, it is usually done so purposely."

That is the basic journey of the song. However, it is worth pointing out that the message of the song is that Bobby is not really ready to make a real connection with all of the sacrifices that this implies. All of the things he lists for what he envisions as a part of this relationship - not with a real person at all, but with an imaginary "someone", which helps to emphasise and reinforce the point - are things that are impossible in a real relationship: to 'keep a tender distance', to 'look not too deep', not 'to give up a thing', to engage in 'just the simple stuff', to be 'always in control' and so on. What he is describing is a fallacy and that is what is represented by the song structure, which doesn't allow Bobby to make the breakthrough he does in "Being Alive". I think this is why it wasn't satisfying as a closing number for the show - at least "Happily Ever After", the first attempt at a song for that spot, was a conclusive statement - and why the placement of the song works when it is used in revivals of the show at the end of Act I.

Also notable in the placement at the end of Act 1 is the "looping" roundabout nature of the song leading in to the show's first temporal "looparound." The song leads Bobby back to his thirty-fifth birthday party again, where we will meet him again twice in Act 2.

It builds up because he wants to take the step but he's afraid.

I'm assuming it just ended with his birthday party after "Getting Married Today." Hrm.

Good question, SLY, haha. My libretto and the Wikipedia article on Company both end Act 1 with "Marry Me a Little."

It's really only very slightly different, with "Marry Me a Little" basically tacked onto what was already there. The scenes following "Getting Married Today" in the respective versions are identical up until the point just after Amy's exit. (The major difference, I suppose, is that the full company sings the lines now rather than the Vocal Minority, which has been eliminated from the more recent productions.)

In the revised version, the company's line, 'We love....' segues into the introduction of "Marry Me a Little". In the original version, Bobby was left onstage alone while the Vocal Minority repeated the 'Bobby, Bobby, Bobby, baby, Bobby, bubi, Robby' once before the orchestra took over, repeating the full phrase twice before repeating the last six notes of the phrase several times, shifting up an octave, alternating the key and finally intensifying the rhythm as the curtain fell.