When is someone ‘too insecure’ to date?

It seems like a number of people don’t want to date someone with low self-esteem or self-confidence, but it feels like that would only be adding to a spiral. I’m one of those people who feels insecure /because/ I have trouble dating. What are your thoughts? Do insecurity and inexperience go hand in hand? Why not date someone who needs a little assurance?
When is someone ‘too insecure’ to date?
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