Yes, I would judge and I'm in the 'I think it's grim' camp.
I know a woman right now, who's 34, who has one DD aged 4. She has had one man after another, 3 to 4 month relationships a couple of times a year for the 6 years I've known her. (No man ever stays with her though, and no man has put a ring on it!) Not sure who the child's father is. I have never seen him, and she never mentions him, she just puts loads of shit on Facebook about how terrible the men are who fuck off and leave the baby mama (and the baby) and never look back.
She's currently got a 'man' living with her who's 19. Fucking 19! He looks 14, and can't even grow facial hair properly. He's a proper cocklodger. He doesn't work, he just sits under the car port smoking weed, and occasionally walks her dog, and mows her lawn ... He's so awkward and doesn't look you in the eye when you speak to him. It's like he is YEARS off being a proper functioning adult. He can't make adult conversation ... No problem shagging though. Her next door neighbour (joined on/semi detached house) says she hears them at it every other night, through the walls, and she can hear her howling like 'Lassie' from Porkys. 34 and 19. Bleurgh!. 😖
I don't know why the hell a 34 year old woman (who's got a 4 year old daughter) has got this man living there ... (She has only known him 5 months and he has lived there for 4!) It's the third man she's had living with her in the last three years, and I actually genuinely worry about the daughter, to be honest with you, with all these random step dads coming in all smoking pot around her/stopping over a lot, and even living with her. And I wonder where the little girl is when they're shagging and she's howling like a banshee!
I think there is really something off about anyone 25+ dating a fucking teenager. Man OR woman. This 34 y.o. woman I know makes my skin crawl. Even her last boyfriend was only 21! (And also a cocklodger.) I don't think she can get a decent man near her own age (with a decent job) to be honest, so she's settling for what she can get.