I don't hear Dolly in Dahlia at all. If you consistently started using quite a different nickname (Lia comes to mind), then I doubt Dolly would ever take anyway.

In terms of Caroline, I think if it's a name you both like then you could learn to ignore that association - hardly anyone else would ever be aware of it, which would make it easier to ignore. I think it goes really well with Annabelle. Of course, giving advice is different to real life because I totally understand your misgivings and would probably have the same funny feelings if I were in your shoes!

I know a lot of people who say Caroline and Carolyn the same, so I can see why the similiarity to the ex-girlfriend would be an issue.  I see Cora on the long list--have you considered Coraline?  Very similiar, but it eliminates the ex-girlfriend issue and I think Coraline and Annabelle work well together.  There is also Rosaline or Rosalyn for a Caroline + Rosa compromise.  

Dahlia-I say it more like Dahl-ya and I don't think the Dolly nickname is obvious.  My guess is the flower association is common enough that most people won't feel like they *have* to resort to a nickname.

Clara & Lucia are both lovely but they do seem a little short next to long/flowy Annabelle.  Of the two, I like Lucia just a tiny bit more for you.

From the long list, Ruby, Violet & Cora are my favorites with Annabelle.  Delia is not a name I care for-I had a great aunt with that name who was called Dealie (as in "lets make a dealie") which kind of ruined it for me.  Naomi and Sabrina are a little dated for me and Maya seems too modern next to Annabelle.  

I think Eleanor could work depending on the nicknames (if you use any).  I wouldn't do Elle and Belle obviously, but I don't see any problem with Belle and Nora or Elle and Anna.  Saying the full names together as Annabelle and Eleanor I do notice the "el" in both, but switching it to Eleanor and Annabelle makes it much less obvious.   Have you considered Eleanora?  The extra syllable makes me notice the matching "el" sounds even less.

Caroline- I have really mixed feelings about this one. On one hand, part of me thinks the statute of limititaions on high school girlfriends ends when you've gotten married, and I agree that if you both love it, you should use it. On the other, I think the circumstances of their relationship and breakup would matter a lot, if I were in your shoes. Did they date all through high school? Did he carry a torch for her after graduation? Was it tumultuous or did they just grow apart? Did they end amicably or messily? If he sees her as an overall positive adolescent learning experience and if he ran into her now, things would be friendly (not awkward or, God forbid, sparks still flew), I would think it was okay.

I don't expect you to give me the answers to these very personal questions, but I think it's important that you answer them for yourself. They might help you come to terms on whether you're ultimately okay or not on giving this name to your daughter.

Cecelia- Lovely. The only problem would be in introducing them, "These are my daughters, Annabelle and Cecelia", something about them together make it a little tongue-twisty, but that's incredibly minor.

Dahlia- I'm not sure how you're pronouncing it. Do you mean DA-lee-ah as in apple, or DA-lee-a as in ball? I wouldn't worry about the Dolly association. It's an almost archaic nn at this pont, and the O and A differences in spelling do a lot to separate them. I also don't think people will automatically nn it, because Dahlia is short and easy enough to say on its own. Weirdly, this one doesn't have tongue-twister factor for me.

Sonia- I agree that it's a bit dated, but mostly I don't like it with Annabelle. Seems too heavy and serious, if you're using the the long O pronunciation; too light if it's the short O.

Clara, Lucia, Rosa- These are nice, but then again, I want something a little substantial next to Annabelle. I don't have any ideas for Clara, but I think Lucinda and Rosamond/Rosalind work really well.

From the rest of your list, I Love Sabrina. I don't think it seems all that dated, although it peaked in the '90s, it's still popular enough that it won't seem out of place among her peers. I think it goes very nicely with Annabelle.

I would imagine once you associate Caroline with your daughter, any similarities will disappear. However, Caroline and Carolyn are really two different names in my mind, plus I could not care less about names of high school exes, so it would not bother me personally. If you have reservations on whether it will still bother you, perhaps hold off.

Of the others, I like Cecilia best and then Dahlia (I don't think Dolly will be an issue). I don't see Sonia as dated. I don't think Corina is dated either, but I prefer Corinne.

I agree with everyone else-- if you don't suggest Dolly, nobody would come up with it on their own.  My sister had a classmate named Dahlia and everyone used her whole name.  Cecelia is a lovely name-- although you might want to ask around to see if anyone has strong associations with the Simon and Garfunkel song, which is an awesome song but not a good association.  Sonia sounds very similar to Sophia to me, making it more modern.  I think it's ready for a come back. 

As far as Caroline goes-- is this woman in the same town as you?  Does your husband keep in contact with her?  Does the association bother him?  If you think the association has faded for those you know and you're ready to make a new association (your beautiful baby girl!) then I'd say it's different enough.  Coraline is a nice alternative, but since it's was recently invented by Neil Gaiman, It doesn't have the same regal sweetness that you love about Caroline.  How do you feel about another version: Charlotte?  or perhapse Josephine would be a good fit?

 Caroline—well, this would depend a lot on the circumstances for me.  "High school girlfriend" doesn't seem like a big deal, but "first love" might bother me, because this makes it sound much more like a serious thing.  But then, the spellings and pronunciations are different, so that does make it a bit better.  I don't know--that's a personal call.    

Cecilia—Very pretty, and a nice match with Annabelle.

Dahlia—I love this one and would throw my vote in for it--an unexpected botanical with a pretty sound and image.  I think it shares Annabelle's sweetness, too.  I pronounce it like Doll-ya, definitely 2 syllables rather than 3 (I say Talia the same way--tahl-ya).  Even so, I wouldn't have thought to change it to Dolly.  I know one adult Dahlia, and to my knowledge nobody calls her Dolly.  It's not a natural and traditional nn for Dahlia (like Ben/Benjamin or Dave/David), so I don't think it would be almost anyone's default.  Honestly, though, a few overly familiar people may try to use Dolly from time to time, and you or she may have to correct them.  I wouldn't think it would be too common, though.  I definitely prefer this spelling over Dalia.

Sonia—I do see it as mildly dated to the 70s-80s, but not in a bad way--it's a sweet, cute name.

Clara--I generally love this name, and think it would go nicely with sis.

Lucia--pretty, but the varying pronunciations throw me a bit, and I do think it will tend to be shortened to Lucy, if that bothers you.  Our neighbors have a young Lucia (loo-CEE-ah), and at first they insisted on her going by the full name, but a lot of people seemed to assume she'd go by Lucy, and eventually the parents started calling her Lucy as well.  Just one anecdote, but thought it might be of interest.

Rosa--seems very Spanish to me, not sure how that goes with Annabelle.  I prefer Rose, or a longer Ros- name (Rosalind, Rosamond, Rosalie, Rosemary).

Corina—maybe a bit dated, in the sense that I don't feel like I've heard of one since the Dylan song (which is Corrina, but I'd say it the same way).  Not sure what to make of it.

Ruby -- nice, and a nice match for Annabelle, if DH comes around

Violet -- see Ruby

Delia  -- prefer Dahlia, which I think has more spark.  Delia feels like a nn to me, I think, for Adelia, even though I know it can be a name on its own.

Eleanor -- love this too, and I don't think the repeated -el- sound with her sister is a problem, particularly because one comes at the beginning of the name, and one at the end.

Eliza -- see Eleanor.  However, it is of course related to your sister's name--maybe you could treat it like a namesake/tribute--it would be kind of a nice connection, if you wanted that.

Well, for me, Carolyn and Caroline are completely different names.

Similar, yes, but different in both sound and overall style and feel imho.

I may be biased, as it's one of my favorite names, and def. the clear winner in my estimation.

I Adore Cecilia. I also love the similar Cecily (sess-a-lee) and just Celia. All seem totally perfect with Annabelle.  Love 'em.

Dahlia-I would pronounce this dawl-ee-ya, with the last two parts sort of running together. I don't love it, and I do think you're going to have headaches with how it's spelled and said, But I don't think Dolly will be an issue at all if that's the only thing holding you back. I also think of the black dahlia murder mystery, but that probably wouldn't be a widespread issue.

Sonia seems entirely different from Annabelle to me. My friend was considering it until her German mil told her that in Germany it would be like naming your daughter Bambi is here (I'm sure this doesn't matter to you-just putting it out there. Her husband is German is why this all mattered....)

Clara-Love it and I think it's Perfect with Annabelle. Same darling, spunky storybook quality. It does seem to be trending upwards.

Lucia and Rosa are darling names, but they seem off with Annabelle. Like they hail from the wrong part of the world.

Corina is just kind of meh for me, and seems like a different era.

Of the longer list, only Ruby and Eleanor seem like good fits. My hesitancy with Eleanor is the utter saturation of Ellas and Ellies near me. Eleanor doesn't seem too close to Annabelle, but the minute someone called her Ellie, it would. If you'd insist on Nora as a nn, then I think it would be great! Ruby is a name I love, and I think it has the same vintage charm and spunk of Annabelle. I'd put it on my short list if I was doing the naming. :)

Good Luck and thanks for letting us all play along!

I'll vote for Louisa because it's a classic that I feel fits well with Annabelle - both in terms of length/gravity and stylistically.