Nat Wolff sat down for a Blind Date with Cosmopolitan’s Editor-in-Chief, Willa Bennett and let’s just say, he kept things real. From attending his ex’s wedding to confessing his biggest romantic fatal flaw to the time a date admitted they were a superfan, Wolff is here to spill. We first fell for Nat back in his Naked Brothers Band days, but this time, he’s all grown up and spilling his best (and worst) dating stories.
Watch 'Play Dirty' out now on Amazon.
Pre-save Nat & Alex Wolff's self-titled record out January 16th here: https://broke.ffm.to/nat-alex-wolff
Stream the single 'Tough' out everywhere here: https://broke.ffm.to/nat-alex-wolff-tough
#NatWolff #AlexWolff #NakedBrothersBand #BlindDate #Cosmopolitan
Watch 'Play Dirty' out now on Amazon.
Pre-save Nat & Alex Wolff's self-titled record out January 16th here: https://broke.ffm.to/nat-alex-wolff
Stream the single 'Tough' out everywhere here: https://broke.ffm.to/nat-alex-wolff-tough
#NatWolff #AlexWolff #NakedBrothersBand #BlindDate #Cosmopolitan
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PeopleTranscript
00:00You know when you see a couple that's posting a lot about each other, you're like, they're about to break up.
00:04It's like the same when you see a couple get tattoos of each other's names, you're like, I give it three months.
00:08My name is Willa Bennett, and today I'm going on a blind date.
00:18Alright, let's go.
00:24So my date's standing me up.
00:26You literally don't have a watch? What's going on?
00:36I'm so sorry that I'm late.
00:38Is this our first date?
00:39This is our first date.
00:40Oh my god, so we know each other, we don't?
00:42We don't.
00:43Oh my god! Okay, fun.
00:45Should we cheers?
00:45Yes.
00:46Hey, cheers.
00:47This is really unconventional.
00:48Wait, what are we supposed to do?
00:50I feel like we have vibes.
00:52So, what do you do?
00:53I'm an actor and a musician.
00:56And I play in a band with my brother.
00:59You probably might know me more as an actor.
01:02I don't know, I was in a show.
01:04This is painful.
01:05This is like when somebody's on the subway and they're like, I know, I know you.
01:08You're famous, right?
01:09Tell me, where have you been in?
01:10And you start listing things that you've been in, and I'd be like, oh, I was in The Fault in Our Stars.
01:14I'm like, I've never seen that shit.
01:15You were in The Fault in Our Stars?
01:16I love that movie.
01:18Jacob Elordi?
01:19Yeah.
01:20Jacob Elordi.
01:20Jacob Elordi's in that movie, isn't he?
01:22Nope.
01:22This is off to a horrible start.
01:24Jacob?
01:25Dylan O'Brien?
01:26No, no.
01:27This is literally my nightmare.
01:29I was like, maybe she won't know who I am.
01:31Keep going.
01:31I can't offend you twice.
01:32Paper Towns was a movie that came out with Carl Delevingne, like, the next year that I was in with her.
01:38My brother and I want to show Nickelodeon a little bit.
01:42What's up?
01:42We have never met.
01:44I'm sorry I said to you.
01:45So Jacob, definitely not in The Fault in Our Stars, but he kind of is tall like Ansel Elgort.
01:52That's who it is.
01:52Who is in The Fault in Our Stars, also not me.
01:53But I am the other guy in that movie.
01:57Maybe you'd say my brother, maybe.
01:59But then I was like, am I going to start listing my brother's credits in order to get to mine?
02:02And I remember my pops was being like, drink slowly, but I'm going to drink quickly.
02:06Drink quickly.
02:06Okay, let's cheers.
02:07Hey, cheers.
02:08Eyes, eyes, eyes.
02:08I'm so happy to meet you.
02:10So happy to meet you, too.
02:11Oh, my God.
02:11Do you read Cosmo?
02:12Hell, yeah.
02:13I remember as a kid it was like really big because there was a lot of sex stuff in there.
02:17So you like to have sex?
02:23What did you say?
02:24Sorry.
02:24You're in Play Dirty, which I know because you're doing a Cosmo shoot.
02:29Do you play dirty?
02:30Tell me about it.
02:30Your questions are, do I like sex and do I play dirty?
02:33I just want to reiterate where we're at.
02:36Tell me about Play Dirty.
02:37They're hard to eat bread, right?
02:40Play Dirty.
02:41Shane Black is the writer-director.
02:44He asked me to do this part with Mark Wahlberg.
02:47He's the one who told me to get an ice plunge because he says it's really good for you.
02:51So I actually did it.
02:52I haven't even told him yet that I got it, but he's amazing.
02:54Where was the ice plunge?
02:55Do you want to tell the story?
02:56He just told me about ice plunges.
02:58He has an ice plunge at his house and he gets up at four in the morning every single day.
03:01Sounds miserable.
03:02And then I definitely don't do the waking up early or anything, but the ice plunge is awesome.
03:05So I learned that from him.
03:06What do you normally talk about on first dates?
03:08Don't you think first dates usually are so awkward?
03:11I like say nothing and I ask a lot of questions.
03:12I know.
03:13Which you think makes you like the cooler person, but it's actually kind of a defense mechanism.
03:17Totally.
03:18And it's kind of boring.
03:19And then someone stands up after him and they're like, wow, I just like talked to you.
03:21It's so long.
03:22And I'm like, yeah, I'm bored.
03:24I did have a horrifying first date.
03:26Tell me.
03:26I showed up to the date and it was a blind date.
03:30We were set up.
03:30We never met.
03:31It was literally us.
03:32And it was you.
03:32And then she thought that I was Dylan O'Brien.
03:34I showed up and she was like already really drunk.
03:37Oh, that's bad.
03:38And she was like, do you know the only reason I'm on this date, right?
03:41And I was like, no.
03:42She was like, because I had your poster on my wall when I was 12.
03:46And I was like, huh, okay.
03:47She's like, does that make you uncomfortable?
03:49And I was like, incredibly, incredibly uncomfortable.
03:52So now is not the time to tell you I had a poster of you growing up.
03:55I couldn't even believe it.
03:56Like, there's no f***ing way.
03:58I didn't.
03:59It was Dylan O'Brien.
04:00It was Dylan.
04:01I'm kidding.
04:01I'm kidding.
04:01Naze Runner.
04:02We really got to stop saying his name.
04:03It's too good for you.
04:04Okay.
04:05This is going to be changing the topic.
04:07This is 1994, the year I was born.
04:12That's the year I was born.
04:13Oh my God.
04:13We're the same age.
04:14There's something in common.
04:15Are you December 17th?
04:16No, I'm September.
04:18So you're a Sagittarius.
04:19Sagittarius.
04:20Do I identify as a Sagittarius?
04:21I identify it if you like it.
04:23Sagittariuses are perfect.
04:24Creative, nice, smart, adventurous, late.
04:30I feel like you're not over the late thing.
04:32We're going to talk about it later.
04:34So this Cosmo is going to be amazing.
04:35I'm going to ask you first date questions.
04:37So if you don't get a call from him after the first date, do you lose your cool or move
04:42on?
04:42Move on.
04:43I agree.
04:44What's your one romantic fatal flaw?
04:46Being so sensitive to other people's feelings that I take it on and then I get resentful.
04:54I'm like mad because they're in a bad mood.
04:57And I'm like, because now I'm in a bad mood, you know?
04:59Whereas I have to have, at least Dr. Sheriff Ostrom, my therapist says,
05:02I have to have some good boundaries and then I can be an even better partner because I
05:06can be, you know.
05:07What else does your therapist say about you?
05:09He loves me.
05:10Really?
05:11He really loves me, I think.
05:13But maybe he's paid to love me.
05:14I don't know.
05:14He's definitely paid to love you.
05:15I know.
05:16So you want to hit on someone at a party that you don't know.
05:19What's your go-to move?
05:20Maybe just to talk to them.
05:22Totally.
05:22Give them a little.
05:23You're just talking to them like a person.
05:24Yeah.
05:24Yeah.
05:25You're five dates in and someone says, I'm not looking for anything serious.
05:27What do you say back?
05:28Have you ever had this where somebody says, like, I'm not looking for anything serious
05:31and you're like, I didn't say that I was.
05:34Yeah.
05:34I hate that feeling.
05:35Because then that means you actually, because you were, kind of.
05:38How about when somebody says, I'm not looking for anything serious, but then they are with
05:42somebody else.
05:42It's just like, maybe this isn't the first, with you, I'm not looking for anything serious.
05:46But then that hurts because you're like, what about me makes it that you don't want to
05:50look for anything serious.
05:50And then you see it on Instagram and you're like.
05:52They're like with somebody else.
05:53And you're like, hey, that looks really serious.
05:56You want to know a crazy one with me?
05:57I went to my ex's wedding.
05:59My first ex, like my first love.
06:00Okay.
06:01How was that?
06:01We stayed friends.
06:02We went to the wedding.
06:03The first second, it was kind of weird.
06:04But then I was like, this is really beautiful.
06:06Did you have fun?
06:07I kind of did.
06:08Yeah.
06:08My brother and I went, we both did get really drunk and we stayed till the very end.
06:12That's iconic.
06:12You're like, I didn't marry you, but I'm the most fun one here.
06:15I'm the most unhinged one here, for sure.
06:17When you're in love, do you broadcast it or play it cool?
06:22Ooh.
06:23Broadcasting it in 1994 was probably really romantic.
06:26Broadcasting it in 2025 is shitty and annoying and Instagram-y.
06:31You know when you see a couple that's posting a lot about each other?
06:35You're like, they're about to break up.
06:36It's like the same when you see a couple get tattoos of each other's names.
06:38You're like, I give it three months.
06:40So you would never put my name tattooed across your head?
06:42I already did.
06:43Nice.
06:44It's covered in heavy, heavy makeup.
06:47But if you did a little bit of, you would see that your name, but it's just Willa.
06:52Or it's just a W.
06:53Oh, you know my name.
06:54What's my name?
06:55Alex Wolfe.
06:56Yeah.
06:56You got it.
06:57Nice.
06:57You get home to a message on your answering machine from an ex.
07:01Classic.
07:01Asking how you are.
07:02Classic.
07:02What do you do next?
07:04Mmm.
07:09If we're eating, we gotta do the napkin.
07:10Mine's been there, sir.
07:12I had an answering machine when I was a kid.
07:13So did you, probably.
07:14It was me.
07:15But.
07:18Waiter.
07:18None of this has ever happened before.
07:20Can I get another fork, please?
07:23Thank you so much.
07:25I'll just go get the, no, just kidding.
07:28That's also never happened to you before.
07:29I'm joking.
07:30Okay.
07:30So you leave it.
07:31I'm no contact with everyone I've ever talked to, so.
07:34You let it go, you call them back the next day and be like, sorry, I was asleep or something.
07:39Like, I missed the call.
07:40Because if they're calling you and saying, I miss you, and maybe they're like drinking,
07:44like maybe they're a little drunk, maybe it's not real, maybe you're gonna get into a conversation
07:48that neither of you is ready to have.
07:49I remember my therapist, go back to it.
07:51Years ago.
07:52I love how much you love therapy.
07:52He's the best.
07:53I would say years ago, I remember him saying like, a conversation before 10 p.m. is okay,
07:58but like after 10 p.m. is a bad idea.
08:00Wow, because of drinking or just timing wise?
08:02No, just timing wise.
08:03Interesting.
08:03It's just too.
08:04When is the right time to introduce your romantic interest to your friends?
08:08Super early on.
08:10If you love your friends, you trust your friends and like think that their opinion matters.
08:13There's a lot of studies right now that are coming out that's the best first, second date
08:17is with your friends.
08:19Like invite them to a friends group because the person you're dating should see you around
08:22them.
08:23I think that's genius.
08:24First date's rough though.
08:26First date's rough too because like you don't know the person and you like want them to,
08:31I don't know, it's not real.
08:32You're not being yourself really.
08:33You're kind of putting on an act, putting on a presentation of who you want them to think
08:38you are.
08:39What's a good first date movie?
08:41Like from when we were kids?
08:43My first, my first date to a movie, I think it was called Wanted and it was with James
08:49McAvoy and Angelina Jolie.
08:52As bullets were flying by, they had a big kiss and I kissed.
08:55That's so cute.
08:56Yeah, around the time.
08:57And the bullets were like and we kissed.
08:59Yeah.
09:02Cheers.
09:03Okay, these are blind reader questions.
09:06Okay.
09:08From Cosmo Readers.
09:09Wait, can we eat the cake?
09:10Yeah, of course.
09:11Should we eat the cake?
09:11Okay, let's see.
09:12Yeah, yeah.
09:12What's a go-to pick-up line that's worked for you?
09:21I've had somebody do a pick-up line to me.
09:23Okay, did it work?
09:23That was really interesting.
09:24It just made me feel really strange for the rest of my life.
09:27They said, you have one really pretty eye and you have one really kind of off eye or some
09:36shit like that.
09:37That's horrible.
09:38That's not a pick-up line.
09:38I'm just like flirting is not an excuse to be mean.
09:41I will say this about Australia and this will definitely get me into trouble.
09:44When I shot Play Dirty, it was like my third time working in Australia and I realized by
09:48that one that if somebody said something like, oh my God, those shoes are like so ugly that
09:53they're like flirting.
09:54I know, I swear to God.
09:56I would just cry.
09:57Same.
09:57And so I would come to set like on the other thing I did this like Tiger King show a couple
10:01years ago where I was literally saying, why is this girl being so mean to me?
10:05Literally, I was like, she hates my outfits every time.
10:08They're like, no, I think that's actually her flirting.
10:10I was like, really?
10:10She's like, no, that's an Australian way to flirt.
10:12But I'm definitely not.
10:13Wow.
10:14Definitely don't know about that.
10:14Yeah, like I'm like, I'm not good at that.
10:16I'm not good at that.
10:16I'm not good at that.
10:17Would you date a fan?
10:19That's a weird question, right?
10:21What would you say?
10:22Can you help me?
10:23I would never date a fan.
10:24Why?
10:25I don't know.
10:26Sounds scary.
10:27What's the worst way you've been dumped?
10:30When I was a kid in sixth grade, I dated a girl named Katie Margulies.
10:34When we were dating for the two weeks we were dating, I got really into the OC because I knew
10:39that she watched the OC.
10:40So I was like, I'm going to watch the OC so I know what she's talking about.
10:43And then she broke up with me in a letter and she wrote, it's too bad that we have to
10:47break up because we both have so many things in common, like how much we love the OC, even
10:51though I just watched it.
10:53And then she drew a picture of me and her and I had a big heart because I loved her.
10:58And she had a heart that just kept getting smaller in the picture.
11:02That's brutal.
11:03Brutal.
11:03And then I ripped up the note and I threw it in the toilet and flushed it and then it
11:07got completely clogged.
11:08And pieces of the letter were just coming out for like a week.
11:11Little pieces of the letter that she wrote.
11:13Did you send her a video?
11:14But I should have.
11:15That's what you should have on TikTok.
11:16Right?
11:16That shit's perfect for TikTok.
11:18Everyone being like, oh my God, me and who?
11:22I have an oddly specific question for you.
11:25Would the Naked Brothers Band perform at my wedding on January 15th, 2026?
11:29Is that a real question from somebody?
11:31Yeah.
11:31Honestly, that would be so fun.
11:33The Naked Brothers Band would probably just be my brother and me.
11:38So you're free on January 15th?
11:40Who do we reach out to?
11:41I don't know about that.
11:42Do you have like NatWolfAgency.com or something?
11:45I feel a little bit like I've been cornered.
11:46Well, why don't you just say you're not sure?
11:48This is like when somebody's at a party and they're like, will you read my script?
11:51You're going to read my script, right?
11:52And I'm like, totally, totally.
11:54I'm like, put your number on my phone.
11:55And then I'm like, why did I say that?
11:57But you don't actually.
11:58But no, no, I'm going to go to the, I'll go to the wedding.
12:00I'll be the best man at the wedding.
12:02You'll be my best man at my wedding?
12:04This is you?
12:07Have you and Alex ever competed for the same love interest?
12:10No, only in a movie.
12:12Oh, really?
12:12What movie?
12:13Stella's last weekend.
12:14Okay, I'm going to watch it tonight.
12:15I'm going to send you pictures of every frame.
12:17From the beginning to the end?
12:19Yeah.
12:19What about scenes I'm not even in?
12:20That's a good question.
12:22What if it's just pictures of Dylan O'Brien?
12:23Do you care if someone writes mean things about you on the internet?
12:28The idea that anybody has said anything mean about me on the internet,
12:31which they have and I have accidentally seen sometimes,
12:34is horrifying and upsetting and puts a pit in my stomach.
12:37So then I just don't read anything on the internet.
12:40Because honestly, even if you read good things about yourself on the internet,
12:42that's toxic too.
12:43None of it is true.
12:45It's not real.
12:46You know what I mean?
12:46Something that's true about you.
12:47That's a good one.
12:49And that's a wrap.
12:50Just kidding.
12:51What's something that's true about me in general?
12:56True about me right now in this moment, I'm feeling really happy.
12:59I had a really good time doing this.
13:00This was awesome.
13:01Oh my god, you're so sweet.
13:02It's true.
13:02I'm so happy to finally meet you.
13:04I know.
13:05Now I'm going to see you everywhere.
13:06I know, constantly.
13:06And I'm going to see you.
13:07Are you here?
13:07You live here?
13:08Yeah.
13:08Or are you living out?
13:09Yeah, we'll see each other all the time.
13:10This is my office.
13:11You live in this room?
13:12Yeah.
13:13With all these, you guys all live together here?
13:16Would you go on another blind date with me?
13:19Yeah.
13:21Checks out.
13:24Checks out.
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