We are expecting baby #2. We don't know yet if it is a boy or a girl. Our first born is a boy named Simon. We love his name but had a hell of a time picking it when he was born.

Our girl name was and still is Annabel. We think Simon and Annabel are perfect for each other and our family (I'm Giselle and my husband is Adam - we think these names have the same vibe as ours without being direct copies). Feel free to comment on the girl name but our issue is actually boy names. The short list contains options that are all over the place from Jasper to Christian (though I now hate 50 Shades for ruining that name) but nothing is really making us as happy as Simon did when we decided on it.

So help Duana, I'm looking for boy name that'll stand on it's own but will fit with his brother’s.

Thanks a ton.

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Do you know my number one favourite thing about people sending in letters?  It’s the implied or actual prerogative of the answerer to point out things that were not the question asked.  Sasha does this all the time:  “And actually, M, you sound a little unglued yourself.”  It kills me.  I love it.

I also love the name Simon.  Think it’s great.  Honestly, it’s one of my favourites.  It’s a known boy name outside the canon of the uber-regular, it translates to other places, languages – it’s hard to go wrong.  So yes, you have your work cut out for you.

That said, here’s my tiny piece of unsolicited advice before the solicited.  I love Annabel too – and I like it with Simon.  I agree with you that they’re easily matched and the exact same amount of recognizable.

But I want you to take a look at the second sentence in your second paragraph.  “Simon and Annabel.”  Now say it out loud.  Now say it out loud three times, as though you’re calling them from the bottom of an escalator they’ve just run up to annoy you.  

Hear it?

Simonananabel.  

That’s a lot of Ns and As.  Is it enough to lose the name over?  Nope – but you’d better call them “Annabel and Simon” a lot to mitigate it.  This is totally possible, just somewhat counterintuitive when Annabel is the younger.  But these are small problems.

Now onto your real conundrum.  I do not think you’ve overstated the problem at all.  Simon’s a hard pea to pod with but I do have a couple of suggestions. I don’t dislike Jasper (though it’s popular) but it doesn’t feel the same – old and new both -  as Simon.  Christian definitely doesn’t feel the same – something about this once totally acceptable name is beginning to feel pastel-neon somehow.  I can’t describe it.  It’s the name equivalent of Pretty In Pink.  It’s Blaine.

So for you, my first instinct was Gabriel.  In addition to being of a similar vintage (and also vaguely biblical, if you care about that), I just feel like Gabriel and Simon have a vibe between them.  Kind of easygoing and ready to take on the world. Adventurers.  Also, they both start with long vowels up front, which I love.  Of course, Gabriel’s quite popular and it practically demands “Gabe” so, if you’re not a nickname person, Gideon comes to mind, though it may be getting a little too bible-licious for you.  

Garrett is underused, and as a result always feels fresh.

Hugo is going to be overused (well…someday) but it has that same great vowel “says its own name” sound and is ADORABLE.  Hugo!

Am I the only one who likes Wallace?  And is this just because Wallace Fennell on Veronica Mars was an easygoing lovable adventurer?

Nigel is also a bit of a Brit-o-phile choice and feels like Simon but the names might also run together.  Simonanigel.  Can you handle it?

Finally, I don’t know why, but I know I have to say it -- Simon and his little brother Otto.  I know Oliver seems safer, but Otto is a loveable scamp who’ll steal Legos and eat cheese sandwiches, and it’s fun to say, right? Please?

It’s enough to make a person want a whole brood.  Sometimes.  Not really.   Please let me know!