She did not "literally" say she regretted it; otherwise those words would literally have been used. Saying "I wish" isn't necessarily regret (being sorry for or ashamed of past actions); here, it's just being sad / upset that the MC also has dumped her, like (the implied) many men of her past. There's a big difference. "I wish I had a boat" doesn't mean you have regret that you didn't buy a boat in the past; it just means that you want a boat now.
Your OBS doesn't make sense to me. All the MC is saying is that he won't judge her for anything in her past. He's not "putting everyone in the same category". What if she said she had shoplifted? What if she said she had hooked? Those are crimes in many places, but I doubt either of those would have turned the MC off, either, if he makes the choice to keep seeing her.
Don't be surprised that I read comments; I don't always respond, but I read a lot of stuff on F95.