Is this a red flag on a first date?

[Iknowaguywhostoughbutsweet]

Went on a date with an old classmate from literally 17 years ago.
He asked me who I'm still in touch with, and I said I'm still good friends with Sarah.
He said "Oh yeah Sarah's really pretty."

He then started talking about another woman called Harriet who is now one of those Instagram models and saying how she is really pretty but that she's so fake online and uses tons of filters.

Like I'm not jealous I don't care that someone thinks other women are attractive it's normal, but spending your first date rating other women we know 🤔

He’s a bore, far too invested in checking out women on IG by the sounds of it, yuck.

Funnily this guy called me ugly at school 🤣 but we were only 14 so I decided to let it go.

Has he called YOU pretty yet?

Not yet 😞

This wouldn’t bother me at all, it’s conversation

I think it would be normal to talk about people you used to know, and some of them will be women, but all focused around their looks? I wouldn't bother with this one

A guy talking about how pretty other women are, when it's in no way relevant to the conversation? OK then.

Rating womens fuckability on your first date?

Chuck this one back.

Yeah it's just odd isn't it. Like he could've said oh what's Sarah up to these days? But straight to her looks instead.

Sounds like he judges women’s worth by how they look. It could also be a triangulation tactic.

Knowing what I know now that would be a red flag for me.

I would trust your spidey senses on this one. Every time I have felt uncomfortable like this it has been for a reason and is your way of protecting yourself. He seems hung up on looks and still in that playground mentality. I had an ex who did the typical "ex was a psycho" and his friend then told me "the only reason he got with her and stayed was because she's so hot, you know a 10" and everything in my body was screaming at me. I should have listened. Men who see women this way don't want the whole person, just the picture.

It's conversation, but not good conversation. Moving swiftly on....

Maybe a teeny bit , but see how he goes if you like him and he is nice to you. Just keep an eye on it but not a straight to sack him comment.

They were talking about old school friends, so I don’t see why it’s not relevant.

He could be nervous and looking for common ground

See how the second date goes

Things like this don't always feel like a big deal on a first date. They can feel just like a bit of conversation, sharing, getting to know you stuff.

But I have found that men who are willing to discuss other women's looks etc on a first date (or at any time really) don't make for the best partners.

It's not always a sign that they will be openly appreciative of you either. Especially not if he hasn't said anything about you so far. Far more likely that you're going to he hearing about these women (and many, many others) through the course of a relationship with him and just end up feeling a bit crap about yourself.

Personally, I wouldn't see him again. Who he fancies shouldn't really be first date conversation material.

If you were talking about old school mates, and she came up in conversation, then I think that’s in context with the conversation.

However, even though he said she was pretty, it does sound like he realises a lot is fake, so it doesn’t actually sound that he’s too impressed with her.

It would be a no from me, because I'm very happy to have a higher bar, because I like being single.
The conversation is incredibly boring for a first date, negative (where does he go to if he's slagging someone off on a first date), show him as someone who judges women based on their looks, and he called you ugly in school!! Absolutely no chance.

It’s boring as fuck conversation.

Sounds pretty dull, if nothing else. Would put me off.

He sounds like he’s still quite wrapped up in high school point scoring and tbh like he’s raging inside that Instagram Harriet wouldn’t date him. Why is it his business if she uses tonnes of filters? Why does it bother him so much that she’s fake, how does it affect him in any way?

I think he probably needs to spend more time asking his date (you) questions and paying you attention, than musing over and judging the many things the pretty girls he’s not with are doing.

He's not improved since school by the sound of things.

Good grief, I'd throw this one back, OP. Shallow and possibly a misogynist.

He's negging you. "They're pretty, but I'm here with you".

He sounds like an immature twat tbh. Give him a miss.