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Pick one of these similar names
Hi there! I am due with a girl in 2 weeks. I have always said I would name a girl Charlotte. However, I grew up with a Top 5 name, and hated being Ashley _. I started to like Scarlett/Scarlet a few years ago, and am considering that instead. My name was #2 and I knew a ton of other Ashleys. My wife’s name was #16, and she knew fewer Kaylas. Do you have any advice?

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I'd go with Charlotte. Don't like the negative association with Scarlett and Charlotte is such a great classic name and the points above re popularity ring true.
Esme Lily makes an excellent point - the amount of people given a popular name is WAY lower now than it was in the 80s and 90s. Charlotte may be in the top five but depending on where you are, there may only be one other Charlotte in your child's grade. I looked at the most popular names in my city last year, and the #1 name was given to less than 90 babies. The #5 name was given to less than 50 babies, I think. In the whole city! That's not very many! People use so many different names now that it's not like it used to be. If you like Charlotte best, I think you should use it.
If this is your first child, it's important that you think about future children as well. Parents often name their children with the same style or a similar style. What type of name are you most attracted to? Are there more traditional names on your girl and boy lists that appeal to you (Charlotte) or do you gravitate to more modern choices (Scarlett)?For me, I usually choose names that are more classic and timeless rather than modern and trendy so I would hesitate to pick Charlotte. Scarlett makes me think of scarlet woman and scarlet fever.And speaking of popularity...when Ashley was on fire in the eighties & nineties, more Ashleys were born at that time than the Charlottes that are born now. For example, when Ashley reached the No# 1 spot in the US in 1991, nearly 44,000 girls were given the name. It was No# 1 again the next year (38,458 girls). In contrast, Charlotte was No# 3 last year and that translates to only 12,596 girls. You really can't compare popularity back in the 80's & 90's to the numbers of today. It's a completely different situation. Parents are choosing a wider variety of names now so even the top names are given to less children. As for Scarlett's figures in 2023, it was No#17 with 6,288 girls. Yes that was basically half of Charlotte's number.Lastly, I would advise you to look up both names on the Social Security Administration (SSA) website. You can do it by state to get a clearer picture.
Scarlett
I had a similar question recently, except it was for a book character. I picked Scarlett because it suited her personality more. For a baby, this isn’t an option. With you and your wife’s names, I feel like Scarlett fits a bit better, but Charlotte would also work. Even if a Scarlett doesn’t know another Scarlett, she will certainly know Charlottes. For a real baby, I would pick Charlotte. If you plan on more kids, think about what style you like. I like Helen and James, and Scarlett would feel like an odd one out. Go with what you like best, and ignore popularity.
I think both a Charlotte and a Scarlett will know lots of people who share their name.