I love the writing Lilit Marcus, who’s revived Jewcy.com.
She comments: "I know that a large part of the reason I am so insecure about my religious identity is because of men I’ve dated and their judgments on my Jewishness. When I was dating a modern Orthodox guy, he considered me "not Jewish enough" because my mom isn’t Jewish, regardless of my level of observance or the depths of my beliefs. [Although, as Julie G. very cleverly pointed out, I am always Jewish enough for people to ask me to chip in for seder ingredients, even if everyone spends the meal telling me I should convert if I want to be taken seriously!] When I dated a secular guy, he called me "too Jewish" because I actually believed in G-d and didn’t just boil Judaism down to matzoh ball soup and holidays. It took a long time before I could define my faith in my terms, and not a man’s. I’m still struggling to decide where I belong (as this post indicates), but I’m a lot more confident than I used to be."
I think other people in these instances can only amplify our own insecurities, not create them. The reason the Orthodox make the non-Orthodox question their legitimacy is primarily because of the gulf in commitment between the typical member of an Orthodox shul and the typical member of a non-Orthodox shul.
Anonymous posts on the same Jewcy thread:
Orthodoxy is like moving to a law-abiding city, after foraging for berries, in constant terror, in the old Wild West. No, it’s not perfect. But it beats wandering around moon-calf, wondering what Jewish time it is, duh.
Is there anything more emotionally dangerous than non-Orthodox dating? The person opposite you isn’t clear what he is, or wants. Meanwhile, your tender little pink heart is both beating to quarters, and, getting older by the minute. Better stay home.
Go to Chabad. Get up to speed. Then see what experienced, trained, people think about your Situation. They can help. Rules can help. Anarchy isn’t as much fun as it’s cracked up to be.