James casually referring to the 2000s as the olden days has shaken me and I don’t know how I’ll recover from it

I want MTV to track some of the contestants of these shows and make them react to themselves in these videos, and watch them clench their teeth from cringing so hard

I worked with Sam a few years ago as a flight attendant. He's actually the sweetest guy and NOT AT ALL like he's portrayed on that show. 100% scripted!

Petition to make ‘Welsh Twins Roast 90s TV’ a whole series. This was genius 😂

Sometimes I wonder why I lack so many memories from the 90's/early 2000s, and I've come to the conclusion that everything was so cringey I've just blocked it all out. These shows being a fine example 😂

When that man came backflipping onto the screen I nearly spat my drink out laughing 😂

"God may forgive you for being gay, but no one will EVER forgive you for that haircut"
Honestly iconic lmao

“Date Me Sittin on a Pencil” was my fave— I can’t believe it got cancelled 😔😔😔

I congratulate you, James and Robert, for being probably the only 2 people on the planet that could persuade me to sit through even the highlights from these shows 🤣. The cringe factor is off the scale 😳😳😳😅. Love you guys x

robert: makeup artist. instant red flag
also robert: *is a makeup artist

The backflip guy reminded me of a date I had once. He randomly says “ I can do a split”. I kind of awkwardly smiled. He said it again. I tried to change the subject. Next thing I know he’s in a full split on my living room floor. Needless to say that was the only date for us. 🤦🏻‍♀️

The shot of the two guys and mum running away hand in hand into the sunset made me call my therapist again cause I can’t recover from that

3:29 The show where the parents pick the dates for the kids is “parental control” and it was based on them not liking their child’s current partner so the mom and the dad would both have a new pick for their son or daughter to replace their boyfriend or girlfriend

"Shes 19...."

Thank you. I don't like when anyone references baseball bats and women sexually. Very creepy vibes tbh

When Robert starts cackling at the guy doing flips. Oh my god my neck hurts from laughing

Oh Boy... As a 44 y/o woman I had MAJOR second hand embarrassment while watching the Date My Mom portion. I don't even have kids!!!!

Eddie was an extremely nice guy though, I like how when she said she doesn't like shopping as much as him, he just said "thats fine! Everyone has their own hobbies"
Very sweet.
Definitely acting though lmao

Where my other Millennials at?? 🥳

"Weekly reminder that we are not the same person"... While both wearing vneck black shirts with white stripes accenting the V... 😂 Good to see you today gentlemen and Ashton. Also, anyone else remember Singled Out?

Life is normal again. James is on my left and Robert is on my right again.😂
Ashton, your captions are on point as usual!😂😂