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  • 6/18/2025
Benito Skinner might show up 32 minutes late to a first date—but trust us, he’s worth the wait. In this episode of “Blind Date," the ‘Overcompensating’ creator and star sits down with Cosmo Editor-in-Chief Willa Bennett for a full 3 course meal and a couple rounds of even more delectable questions. Between sips of a spritz, Benito opens up about his thoughts on monogamy, make-or-break dating habits, and the status of his relationship. He credits Cosmo for raising him into the “nasty boy” he is today, but will he head back to Willa’s place after their date? Only if he can check out what's on her bookshelf, first.

Stream ‘Overcompensating’ on Prime Video.

#BenitoSkinner #BennyDrama #Overcompensating #BlindDate #Cosmopolitan

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People
Transcript
00:00Would you want to come back to my place?
00:02Yeah, absolutely.
00:03I would love to see what books you have.
00:04My name is Willa Bennett.
00:06I'm the editor-in-chief of Cosmo and Seventeen,
00:08and this is Blind Date, where I go on blind dates
00:11with my celebrity friends.
00:12And I have to guess who it is?
00:14Pedro Pascal.
00:15You're thinking people out of a way cooler than me.
00:17I will be pulling from old Cosmos
00:19and exploring the intricacies of love and relationships.
00:22Name three turn-ons in a relationship.
00:25Likes me.
00:27Would you ever look through someone's phone
00:28that you're dating?
00:29Hell yeah.
00:30Horny little minxes, these Cosmo readers.
00:34What is the first thing you notice
00:35about someone you're interested in?
00:36Face, next question.
00:50Anyone know if they're coming?
00:55Should I just leave?
00:59We don't know?
01:00They're doing touch-ups, so you may have this actual order.
01:10Why did you almost stand me up?
01:12What the heck?
01:13I didn't.
01:13Who's saying this?
01:14I was in glam.
01:16Okay, so you're really famous if you have glam.
01:18No.
01:20Oh.
01:22Okay.
01:23Take it in that salad.
01:24Don't let me keep you.
01:25Take it in that salad.
01:26Are you a really famous actor?
01:27No.
01:28Maybe if you hear me eat a grapefruit, you'll know who I am.
01:32Yeah, I want to listen.
01:32Let's see.
01:34Mmm.
01:35Got this on mic.
01:39Have we met before?
01:40Yes.
01:41Whoa.
01:42That was a really strong yes.
01:43You love me.
01:44I love you.
01:45Yeah, you're totally obsessed.
01:46Because I have a crush on you.
01:48Well, who's to say?
01:50Are you my type?
01:51How do I say this?
01:53No.
01:54Tell me what you do for a living.
01:55I am an actor, a writer.
01:59Barry Keoghan.
02:00Yes.
02:01No, sorry, unfortunately, it's going to be a huge letdown
02:04when you realize I'm not famous.
02:06That's going to rock your world.
02:07You're like a TikToker, maybe?
02:09Well, yeah, I dabble in the fine arts.
02:11I feel like we're having chemistry right now,
02:13even though you were late.
02:14You are kind of blushing.
02:15Whoa.
02:16Whoa.
02:17I feel like we're on a real date.
02:19You're making me laugh, so you must be funny.
02:21Sometimes.
02:21Sometimes.
02:23Oh, that's good.
02:24Where's the salad home?
02:25What's good about it?
02:26Girls, don't talk to me like that.
02:29You might get a second date if you act like that.
02:31Are you James Charles?
02:33Oh my god, I wish.
02:36If I was sitting right now with a cut crease talking
02:38to you like this, yeah, I wish.
02:41No.
02:41Matt Rogers?
02:43Oh, you're really getting closer.
02:45And you're really, really funny.
02:46Not only.
02:48Benny Drama.
02:49Oh my god.
02:50Sexy.
02:51You did it.
02:51You did it.
02:52Come here.
02:52That was tough.
02:53Wait, come here.
02:54Aw.
02:55Oh, wow.
02:56Hi.
02:56How are you?
02:57Oh my god, you look amazing.
02:58Wait, where's it?
02:59This is for you.
03:00You look so cute.
03:01That is literally my love language.
03:02I'm not even mad anymore.
03:03I know.
03:04Overcompensating looks amazing.
03:05Tell me how long you're working on it.
03:07You've been writing it for a while.
03:08Like six years.
03:09And it's inspired by your comedy special that you were doing
03:12in New York, right?
03:13Yeah.
03:13I have never been so proud of something, ever.
03:16And it's also like, it is kind of my life, but also not.
03:19And I feel like I made enough separation between myself
03:21and the character where I don't feel too, like,
03:24strange watching it.
03:26Yeah.
03:30This is incredible.
03:32Before we transition into the second course, which is
03:34where I'm going to go to September 1997 and ask you
03:37first date questions from Cosmopolitan, if you could pick
03:40one cast member to go on a date with, who would it be?
03:43Owen Thiel, I do just go on dates with.
03:45So that's kind of cheating.
03:46You guys would be really romantic.
03:48Should I leave Terry?
03:50Oh my god, how the-
03:51Done leaving him.
03:52How's Terry?
03:53He's so good.
03:54We've been together nine years.
03:55Are you going to propose?
03:57I am currently playing 19 on screen.
04:00So yeah, really soon.
04:04Wait, really?
04:04I feel like we talk about it.
04:06Does Cosmo have the exclusive?
04:07Exactly.
04:08Tell me everything.
04:08Of course.
04:09We're both very busy right now.
04:11So as much as my schedule is random and I don't know
04:14what I'm doing, he also doesn't know what he's doing.
04:16So I don't know if he can make it to the wedding,
04:19but we're going to think about it.
04:21OK, so we have a Cosmo quiz, even though I'd
04:23look into your eyes all day.
04:24I know.
04:24OK, so these are what?
04:26Cosmopolitan September 1997.
04:28I should ask you on a first date.
04:30My sister got Cosmo, and this is what I did as a kid.
04:32She would do these quizzes with me.
04:34So would you say you're prepared?
04:35That's why I'm filthy.
04:37That's why I'm a nasty boy.
04:39Are you religious?
04:41Not at all.
04:42Because I'm a man of God.
04:43Yeah.
04:44I'm a man of the cloth.
04:45What do you like to do in your spare time?
04:47It's funny.
04:47I think sometimes because of the work I do, people are like,
04:49you love to be crazy.
04:51And I really don't.
04:52I love to just be at home with Terry watching a show
04:54and he's asleep.
04:55That's heaven to me.
04:57Would you want to come back to my place?
04:58Yeah, absolutely.
05:00I would love to see what books you have.
05:01Ooh.
05:03I bet you run the gambit.
05:04I'm not like other girls.
05:05I know.
05:05I'm different.
05:07Do you think people are naturally monogamous?
05:10Oh my god.
05:11That's in Cosmo?
05:12OK, relax.
05:15Here's the thing.
05:16I think it really ranges from person to person.
05:18Every person I enter, I have been in relationships with
05:21or had things with, I feel like everyone
05:22has their own take on that.
05:23Wow.
05:24I personally like being monogamous, but I
05:27think my thing is I truly don't care what anyone
05:30else wants.
05:30I want them to be happy in whatever they want.
05:32But I don't think I could be with someone who wasn't down
05:34to just be with me.
05:35I can't share.
05:36Yeah, you can't share.
05:37I can't share anything.
05:38And I'm feeling jealous that you're talking
05:40about another person with me, so.
05:41Sorry.
05:42Every man I've gone on a date with recently
05:44hasn't really been excited by me.
05:46What feedback do you have on me?
05:47Totally gay.
05:47They're gay.
05:48Yeah, they're gay.
05:49It's not you.
05:50Next.
05:50Do you think it takes depth to maintain
05:52a dedicated relationship, or can two people who are surface
05:54level make it work?
05:55No, you need depth.
05:56You got to get below that waterline.
05:59You really got to know each other.
06:00But what if two people don't have depth?
06:02I think that, like, you have to find someone on your level.
06:05You're talking about actors?
06:07I think if you wanted to play it like that, I just don't know
06:10if it would last a long time.
06:11I think past, like, a couple years if you've only been
06:14surface level.
06:15That seems crazy to me.
06:16Come on.
06:17Open up.
06:18Let me hear about your childhood traumas.
06:20Would you sleep with me on the first date?
06:22I have been known to do everything but that on a first date.
06:27Wow.
06:27Yeah.
06:28But you know what?
06:28Who knows?
06:29Maybe I'll change it for you.
06:30You will.
06:31Literally.
06:32Stop.
06:38So special.
06:39Oh.
06:40I ordered this.
06:40No.
06:42This is my favorite.
06:42Did you know?
06:43Of course.
06:45OK, these are blind questions that I have not seen because I
06:47didn't know you were, obviously.
06:48I can't wait.
06:49Yeah.
06:49What's your biggest turn off in a relationship?
06:51Moodiness.
06:53Oh, interesting.
06:53I have this thing where I think moods are for kids.
06:56It's kind of like, you know, it's just like throwing a fit.
06:59It just feels childish.
07:00Who's the most famous person who's hit on you?
07:03Oh my god.
07:05I got that.
07:06OK.
07:07Wait, this is so hard.
07:08My publicist is sweating.
07:10I did meet Cameron Diaz, and I wouldn't say she hit on me,
07:13but she was like, you and Terry are really cute.
07:15And like, I'll take that.
07:16I'm going to take that as she hit on me.
07:18What's the worst way you've ended things with somebody?
07:21Oh, a text.
07:22But here's the thing.
07:23He voted for Romney.
07:24Next.
07:26I had my reasons.
07:27Yeah.
07:28What's one thing that you've lied about on a date?
07:30I mean, definitely plans after and then just gotten out of
07:34there.
07:34I just feel like, don't, we shouldn't waste our time.
07:36Who's paying tonight?
07:38Me.
07:38Really?
07:39I hate splitting, and I think it's weird.
07:41Wow.
07:41I don't want to deal with it.
07:42But what if I want to pay?
07:43Then go for it.
07:44Just don't let me see.
07:45What's the sexiest thing someone can say to you on a first date?
07:49And have I said it?
07:50You have nice skin.
07:52You have really nice skin.
07:53Done.
07:54I'm on my back.
07:55Done.
07:56Take it.
07:56I will accept this rose.
07:58It is.
07:59You do look gorgeous.
08:00Thank you so much.
08:00So do you.
08:01How quickly have I said I love you in a relationship?
08:04Oh, I think I told Terry I loved him, like, date three.
08:06You're falling for me.
08:07I literally am.
08:08How did you know?
08:09Yeah, sorry.
08:09Will you go on another date with me?
08:10Yeah, done.
08:11OK, romantic.
08:12Then where are we going?
08:13Terry's house.
08:14Done.
08:14I love it.
08:15You've got to come to his wedding.
08:16It's going to be amazing.
08:18Do we cheers?
08:43o'
08:51Do you wait?
08:52No, no, no, no.
08:53Do you, man.
08:54Oh, no.
08:54Oh, you, man.
08:55Do you, man.
08:55Do you, man.
08:56Do, man.

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